Windows to macOS conversion

[bladerunner714]

Apologies if I've selected the wrong forum; this is my first post here.
I'm planning the conversion of my mature Windows installation to macOS. A summary of my conversion plan is attached below.
Any comments or advice will be very much appreciated.

Conversion Plan Summary
Objective: Convert a mature Windows 7 installation to macOS.
The user: Retired systems and network manager. Early experience with Apple Lisa with MacWorks and Macintosh Plus with HD20; twenty-five years with Microsoft Windows from Windows 3.0 through Windows 7. Current experience with iPhone 6S Plus.
The installation: Three Windows 7 systems on a secure, private LAN. Storage includes twenty-five year archive of personal files including financial records, correspondence, digital images, music and miscellaneous documents of all kinds. Substantial commitment to Outlook 2003 POP3 e-mail client, Calendar and Task Manager, Word, Excel, Quicken and Photoshop.
The philosophy: Build a macOS installation to provide functionality similar to the existing Windows 7 installation. Key to the conversion is NOT to match application for application but to implement the required functionality.
The plan: Install a Mac mini of sufficient capacity to be run side by side with the main Windows 7 system. This should allow the two systems to share an exiting 27 inch monitor through an HDMI switch, to share files across the network and to provide a backup facility for the Mac using existing (but not shared) USB-3 external drives. Conversion can then be managed at a comfortable pace, function by function, until the Windows 7 system(s) are no longer needed.

 

[honestone]

Hi bladerunner714, and welcome! You actually did post in the correct forum. We will try and help you.

From what I am gathering, you will eventually be completely on the Mac OS. I have a late 2012 Mac Mini myself, and the machine works fine. However, shortly after purchasing it, I swapped out the slow, 1 TB 5400 rpm internal drive (eventually went inside a nice, slim Orico external enclosure) for a fast, Samsung 840 Pro 256 gig SSD. Talk about a significant speed boost! I also have a 1 TB Seagate External drive connected to my Mac Mini via a Firewire 800 connection. However, recently my other 1 TB Seagate External drive started going bad, and I have subsequently replaced it with a Samsung 850 Pro 512 gig SSD, enclosed in another Orico external case. I use it mainly for backups, and when I do connect it, it is via USB 3.0. But, when I do make backups, it is 3 times as fast to the SSD as it is to the Seagate drive (spins at 7200 rpm). I plan on replacing that "good" Seagate drive with another Samsung 850 Pro. I am just deciding on the size.

From a software perspective, are you going to start with OS 10.12.1, Sierra? That is the latest Mac OS. I have not read about any serious issues with it. You'll just need to make sure that you obtain the correct versions of any third party software you plan on using (more on that below), for Sierra compatibility. I though am waiting to upgrade from OS 10.11.6 (the latest (and last) version of El Capitan), as one of my critical applications has not been updated yet for OS 10.12 compatibility. As you can imagine, Macs have come a long way since the Apple Lisa and Macintosh Plus days, and especially on the software front. If you only use Quicken for "basic" checking (and possibly Bill Paying and/or uploading and downloading transactions), Quicken 2007 should be OK. It's the one I have been using, but I only use it as another check register (I have free On Line Bill Pay with Wells Fargo, and I don't need to upload or download transactions). But if you need something more sophisticated, you should consider Quicken 2016.

For Office software (and especially Outlook), here are my experiences. I have been using Office 2011 (and Outlook 2011 for my EMail needs) for about 4 years or so. Never had any issues with reading Windows-based Word and Excel files into Word 2011 and Excel 2011 on the Mac. Outlook 2011 has always worked well for me (my ISP is Comcast), and I am "connected" via POP3. However, as I suspect you know, Microsoft tends to drop support for older products, and the Office Suites for Macs are no exception. They dropped support for Office 2008 for the Mac about 2 or 3 years ago, and I suspect it's just a matter of time before they drop support for Office 2011. So, I recently obtained Office 2016 for the Mac, and when I first booted up Outlook 2016, it did a super job of importing all my "stuff" (EMails, ISP accounts and settings, etc.) from Outlook 2011. I can only assume that it should work the same in your case, exporting all the "stuff" from your Outlook 2003 "setup". As expected, Word 2016 and Excel 2016 work real well (cannot comment about Calendar and Task Manager).

The other things you need to plan for are 1) disk cleanup, maintenance, and repairs, and 2) backups. As one would expect, there is such functionality "built" into the Mac OS, but there are third party products that are either more "effective", or superior. Myself, I use SuperDuper! for my weekly backups, and it creates a bootable backup/clone. I have needed (on some rare occasions) to recover from a "disaster", and doing it via SuperDuper! was/is a snap. Such bootable backups also are real handy when I need to do an OS upgrade (like I'll do shortly in "moving" from OS 10.11.6 to OS 10.12.1). And, I have both TechTool Pro (that is the one I am waiting on for Sierra compatibility) and Disk Warrior for my disk maintenance and repair tasks. Either of those products do a much better job than Disk Utility, which comes with the Mac OS. (I also use an excellent freeware program called Onyx which has some valuable and useful features too).

By the way, Micromat, the developer of TechTool Pro, tends to have a sale on TechTool Pro around this time of the year (actually around, or just after, Thanksgiving). It normally sells for $99.99 (Disk Warrior is about $10 more), but I have seen it for $39.99 this time of the year. Also, sometimes one can purchase a "bundle" of Mac software for an inexpensive price, and TechTool Pro is included as part of the bundle.

I'm sure you'll receive other helpful suggestions from other folks around here. We have a great "bunch" of folks here, and you have come to the right place!

So, welcome again!

 

[bladerunner714]

Hi bladerunner714, and welcome! You actually did post in the correct forum. We will try and help you.

From what I am gathering, you will eventually be completely on the Mac OS. I have a late 2012 Mac Mini myself, and the machine works fine. However, shortly after purchasing it, I swapped out the slow, 1 TB 5400 rpm internal drive (eventually went inside a nice, slim Orico external enclosure) for a fast, Samsung 840 Pro 256 gig SSD. Talk about a significant speed boost! I also have a 1 TB Seagate External drive connected to my Mac Mini via a Firewire 800 connection. However, recently my other 1 TB Seagate External drive started going bad, and I have subsequently replaced it with a Samsung 850 Pro 512 gig SSD, enclosed in another Orico external case. I use it mainly for backups, and when I do connect it, it is via USB 3.0. But, when I do make backups, it is 3 times as fast to the SSD as it is to the Seagate drive (spins at 7200 rpm). I plan on replacing that "good" Seagate drive with another Samsung 850 Pro. I am just deciding on the size.

From a software perspective, are you going to start with OS 10.12.1, Sierra? That is the latest Mac OS. I have not read about any serious issues with it. You'll just need to make sure that you obtain the correct versions of any third party software you plan on using (more on that below), for Sierra compatibility. I though am waiting to upgrade from OS 10.11.6 (the latest (and last) version of El Capitan), as one of my critical applications has not been updated yet for OS 10.12 compatibility. As you can imagine, Macs have come a long way since the Apple Lisa and Macintosh Plus days, and especially on the software front. If you only use Quicken for "basic" checking (and possibly Bill Paying and/or uploading and downloading transactions), Quicken 2007 should be OK. It's the one I have been using, but I only use it as another check register (I have free On Line Bill Pay with Wells Fargo, and I don't need to upload or download transactions). But if you need something more sophisticated, you should consider Quicken 2016.

For Office software (and especially Outlook), here are my experiences. I have been using Office 2011 (and Outlook 2011 for my EMail needs) for about 4 years or so. Never had any issues with reading Windows-based Word and Excel files into Word 2011 and Excel 2011 on the Mac. Outlook 2011 has always worked well for me (my ISP is Comcast), and I am "connected" via POP3. However, as I suspect you know, Microsoft tends to drop support for older products, and the Office Suites for Macs are no exception. They dropped support for Office 2008 for the Mac about 2 or 3 years ago, and I suspect it's just a matter of time before they drop support for Office 2011. So, I recently obtained Office 2016 for the Mac, and when I first booted up Outlook 2016, it did a super job of importing all my "stuff" (EMails, ISP accounts and settings, etc.) from Outlook 2011. I can only assume that it should work the same in your case, exporting all the "stuff" from your Outlook 2003 "setup". As expected, Word 2016 and Excel 2016 work real well (cannot comment about Calendar and Task Manager).

The other things you need to plan for are 1) disk cleanup, maintenance, and repairs, and 2) backups. As one would expect, there is such functionality "built" into the Mac OS, but there are third party products that are either more "effective", or superior. Myself, I use SuperDuper! for my weekly backups, and it creates a bootable backup/clone. I have needed (on some rare occasions) to recover from a "disaster", and doing it via SuperDuper! was/is a snap. Such bootable backups also are real handy when I need to do an OS upgrade (like I'll do shortly in "moving" from OS 10.11.6 to OS 10.12.1). And, I have both TechTool Pro (that is the one I am waiting on for Sierra compatibility) and Disk Warrior for my disk maintenance and repair tasks. Either of those products do a much better job than Disk Utility, which comes with the Mac OS. (I also use an excellent freeware program called Onyx which has some valuable and useful features too).

By the way, Micromat, the developer of TechTool Pro, tends to have a sale on TechTool Pro around this time of the year (actually around, or just after, Thanksgiving). It normally sells for $99.99 (Disk Warrior is about $10 more), but I have seen it for $39.99 this time of the year. Also, sometimes one can purchase a "bundle" of Mac software for an inexpensive price, and TechTool Pro is included as part of the bundle.

I'm sure you'll receive other helpful suggestions from other folks around here. We have a great "bunch" of folks here, and you have come to the right place!

So, welcome again!

Hi and thanks for your help!


You're right, I'll eventually be completely resident on the Mac and off the PCs although the process may take a year or more. My Mac mini will come with the 1TB internal SSD. I'll use conventional external HDs on USB 3 for backup only because I already have them available. And yes, I'll start with OS Sierra.


I'm pretty much a power user of Quicken and already using the 2016 Premier version on Windows. I'll probably start with 2017 on the Mac.


A major advantage of my side by side approach is the ability to 'try it and see' when looking for solutions. And I should mention that my escape from the PC platform is not just from Windows but from Microsoft in total. Accordingly, I will not use Office. Also I may exercise some bias in favor of native Apple software.


Since I plan to replace functionality, not applications, the functionality now provided by Office may be served by more than one solution on the Mac. For example, I've already begun tinkering with Apple's Mail program on my iPhone and I'll probably try others like Pages, Numbers and so on. And there're other suites like Libre etc, etc.


Backup is a first priority for me and I'll probably start with time Machine. But I've learned the value of image or bootable, clone type backups and I appreciate the tip about SuperDuper.


Thanks again for your help and you can be sure I'll be back looking for suggestions and advice as the process moves forward.

 

[honestone]

You're most welcome! I'm glad that I can be of assistance.

Yes, it looks like you will need to go with a more "advanced" version of Quicken for the Mac. Also, I am actually pleased with Microsoft Office suites for the Mac. When I was working as a software developer, I did need to use the Windows versions of Word, Excel, and Outlook, and I never had any complaints about them. But again, I was using them as a user, not as a developer. Hence, I can understand where you are coming from.

Glad you understand the value of backups. Too often, Mac users believe that Macs are "immune" to issues, and thus don't perform backups. Of course, they are asking for trouble by ignoring backups. The same is true of disk cleanup, maintenance, and repairs. As I mentioned, there are a couple of third party products that are superior to Appel's Disk Utility, an dI would strongly recommend that you purchase at least one of them (two would be better!).

One of the most helpful members here, Cory Cooper, uses a third party suite like you mentioned. It might even be Libre, but I am not sure. I am sure he will "chime in", as he is very knowledgeable and helpful.

I will say one thing, though. I do see quite a few posts from users about issues with Apple's Mail Program. Unfortunately, I don't have much (if any) first hand knowledge with that program. Another one you might look at is Thunderbird. It is free, and it is from the group that develops Firefox.

Finally, I suspect you already know that traditional external hard drives have a life span of between 5 and 7 years (depending on use, care, etc.). I would definitely recommend that if you ever need to replace any of them, SSDs are the way to go! As I mentioned above, I now have a Samsung 850 Pro 512 gig SSD inside a nice, slim Orico external case. After I did my backup for each of my machines, via SuperDuper!, to separate partitions on the drive (took 1/3rd the time compared to backing up to my traditional Seagate (7200 rpm) drive), when I booted each of my Macs from those backups, it was fast!

 

[bladerunner714]

You're most welcome! I'm glad that I can be of assistance.

Yes, it looks like you will need to go with a more "advanced" version of Quicken for the Mac. Also, I am actually pleased with Microsoft Office suites for the Mac. When I was working as a software developer, I did need to use the Windows versions of Word, Excel, and Outlook, and I never had any complaints about them. But again, I was using them as a user, not as a developer. Hence, I can understand where you are coming from.

Glad you understand the value of backups. Too often, Mac users believe that Macs are "immune" to issues, and thus don't perform backups. Of course, they are asking for trouble by ignoring backups. The same is true of disk cleanup, maintenance, and repairs. As I mentioned, there are a couple of third party products that are superior to Appel's Disk Utility, an dI would strongly recommend that you purchase at least one of them (two would be better!).

One of the most helpful members here, Cory Cooper, uses a third party suite like you mentioned. It might even be Libre, but I am not sure. I am sure he will "chime in", as he is very knowledgeable and helpful.

I will say one thing, though. I do see quite a few posts from users about issues with Apple's Mail Program. Unfortunately, I don't have much (if any) first hand knowledge with that program. Another one you might look at is Thunderbird. It is free, and it is from the group that develops Firefox.

Finally, I suspect you already know that traditional external hard drives have a life span of between 5 and 7 years (depending on use, care, etc.). I would definitely recommend that if you ever need to replace any of them, SSDs are the way to go! As I mentioned above, I now have a Samsung 850 Pro 512 gig SSD inside a nice, slim Orico external case. After I did my backup for each of my machines, via SuperDuper!, to separate partitions on the drive (took 1/3rd the time compared to backing up to my traditional Seagate (7200 rpm) drive), when I booted each of my Macs from those backups, it was fast!

Thanks again. You're right about hard disks. I'm just using mine up. They will be replaced with SSDs as they're retired.

 

[honestone]

I forgot to mention one thing about SuperDuper!. There is another, similar product on the market called Carbon Copy Cloner. Both of them make bootable, backup/clones of what you are backing up, but Carbon Copy Cloner also backs up the (hidden) Recovery HD partition, whereas SuperDuper! does not. That partition gets installed whenever one does a clean, "virgin" installation of the Mac OS. This link describes how to get to that partition, and what its capabilities are:

https://support.apple.com/en-us/HT201314

In my case, this partition is actually not necessary (unless I have a MAJOR catastrophe with my backups), as 1) I can boot to my SuperDuper! backup and access Disk Utility from there, 2) I have two superior disk maintenance/repair programs in TechTool pro and Disk Warrior, and 3) I can do a clean, "virgin" installation of the Mac OS from the backup. Of course, if I do #3, I would first launch Disk Utility and Erase and Format (not necessary in my case, but for others, also Partition) my SSD.

Additionally, the Recovery HD partition can be easily created, if need be.

Assuming you purchase your Mac MIni brand new, inside the Applications folder, there should be a file entitled "Install macOS Sierra". You need to make a copy of that file in another location, as if you launch it from the Applications folder and perform the installation, that file goes away, and thus having another copy is crucial. (Not sure why, but whenever I have launched a similar one for any prior OS from my backup, and it is in a different location, it does not go away).

Here are the links for SuperDuper! and Carbon Copy Cloner:

SuperDuper!: http://www.shirt-pocket.com/SuperDuper/SuperDuperDescription.html

Carbon Copy Cloner: https://bombich.com/

As you can see, SuperDuper! costs $27.95, whereas Carbon Copy Cloner costs $39.99.

 

[bladerunner714]

Thanks for the information. My Mac should be here in a week or two and backup is the first priority for me.

 

[bladerunner714]

Hi honestone!

Thanks again for your help with my Windows to Mac conversion. I have an update on my progress and a request for a little more advice.

The conversion has gone extremely well so far and much faster than I anticipated. My Quicken database converted nicely from Windows to Mac and I find the Mac version easier to use. After climbing a small learning curve, it seems to me that LibreOffice is far superior to the Microsoft Office 2003 I’d been using on the PC. All of the functionality of Windows Outlook has been converted to a combination of native Mac apps and a robust task manager called OmniFocus. I just purchased and installed the Mac versions of Adobe Photoshop Elements 15 and Adobe Premiere Elements 15 so my digital imaging is covered.

I’m at the point now where I’m moving large amounts of archived data from the PC to the Mac and I would appreciate some experienced advice on managing my storage.

My Mac mini has a 1 TB SSD for internal storage. I have Time Machine running its default automatic protocol on an always connected 4 TB Buffalo DriveStation 7200 RPM External Hard Drive and Carbon Copy Cloner 4 running ad hoc and daily scheduled clone operations to a similar, always connected, Buffalo DriveStation but with 2 TB capacity. In addition I make frequent clone operations to a rotation of three 1 TB Buffalo MiniStation and Western Digital My Passport Portable External Hard Drives kept offline with one in a safe deposit box at the bank. As previously mentioned, backups are a priority for me and I think my scheme gives me pretty good protection against the occasional “Oh Shit!” kind of problem as well as against most catastrophic failures.

My question regards Disk Warrior. If I understand what I’ve researched, the product is intended to be used as a maintenance tool to watch for and correct any corruption in the hierarchical file / folder structure before it results in a loss of data. Alsoft wants $120 for a new license and it’s certainly worth it to me if it’s necessary to protect the integrity of my archives. I have extensive experience with failure recovery in the Windows environment but it always involved either hardware failures or corruption induced by errant software. The directory corruption I‘ve read about in the Mac environment is new to me.

Would you say my understanding of the product is substantially correct and do you have any particular experience or advice you can share about the product and/or the kind of problem it’s intended to protect against?

Thanks
RW

 

[honestone]

Glad everything is working out well. Also, you certainly value backups! And Carbon Copy Cloner is an excellent choice for that.

As far as Disk Warrior is concerned, yes, the functions you are reading about are definitely valid. However, I have been using TechTool Pro for a number of years, and it has always served me well (I also use Onyx together "with" TechTool Pro, and it is free!). TechTool Pro also can help in watching for, and correcting, corruption in the hierarchical file / folder structure. It also does a lot of other, useful tasks. And it costs less than Disk Warrior, $99.

Of course, I am a "stickler" for keeping my Macs "lean and clean", but it does take some effort. Still, by doing daily disk cleanup on my own, and weekly disk cleanup/maintenance/repairs, and backups (by using Onyx, TechTool Pro, and SuperDuper!), I rarely encounter issues. Additionally, whenever a new Mac OS comes out, I do not "upgrade in place". I do my weekly tasks mentioned above, re-boot the machine from the (just completed) SuperDuper! backup, use Disk Utility there to Erase and Format my internal drive (SSD), perform a clean, "virgin" installation of the new OS, and finally use Migration Assistant to "migrate"/copy needed "stuff" from that SuperDuper! backup. I then re-boot my machine, and I am in business. I follow all of that for both of my Macs, and it has always served me well.

I think Disk Warrior is an excellent program, and it does (primarily) one thing, and one thing well: as you stated, it watch for and correct any corruption in the hierarchical file / folder structure before it results in a loss of data. But TechTool Pro can do that also, along with other tasks. Disk Warrior (at least to me) is useful if one does not do much "regular" maintenance, and I have read where it can correct some real "obscure" problems. You cannot go wrong with either one.

 

[bladerunner714]

Thanks again honestone. Your protocol for OS upgrades sounds well considered. I'll make a note of it. I'll do some more research to help me choose whether Disk Warrior or Tech Tool Pro will be a better fit for me. RW

 

[honestone]

One important thing I forgot to mentions is the following. Before Sierra was first released, Apple had already announced that it was going to change its file system (ie, the Finder), and that was going to happen during the first half of 2017. I expect such a change will be via an OS upgrade "within" Sierra, and not via the next OS (Apple typically releases new OSs in September). Such a change will, most likely, have a tremendous impact on software, and especially for disk utility software like Onyx, Disk Warrior, TechTool Pro, Drive Genius, etc. For myself, I have at least 5 critical apps that would need to be upgraded for such compatibility before I upgraded. There might even be more. I am also thinking that for disk utility software, such upgrades will not be free. We'll see.

 

[bladerunner714]

Interesting - how should I expect to be notified?

 

[honestone]

I am positive it will be "all over" the internet, especially on Apple-specific sites (like www.macworld.com).