I assume you started with the initial release of Sierra, OS 10.12. There have been two subsequent updates, the most recent being OS 10.12.2. Strange that everything was fine the first time you booted up, but issues on subsequent tries. When you booted to the (hidden) Recovery HD partition, what happened regarding the monitor?
Also, when you upgraded from Yosemite to El Capitan, did you do "an upgrade in place"? That is, without doing an Erase and Format of your internal drive, then a clean, "virgin" installation of El Capitan? Similar question when you upgraded from El Capitan to Sierra.
Myself, for both of those upgrades, I did not "upgrade in place". I first did one final "cleaning" of each prior OS, then did my (normal) SuperDuper! backups to two external devices. I then re-booted from the backup (SuperDuper! makes a bootable backup/clone. It's almost like having another machine!), used Disk Utility there to Erase and Format my internal drive (SSD), did a clean, "virgin" installation of the new OS, and finally used Migration Assistant to "migrate"/copy needed stuff from the backup to the internal SSD. (Migration Assistant is offered right after the completion of the OS installation). I then re-started from the internal SSD, and I was in business. I did this for both of my Macs, and for both of the most recent OS upgrades, ie, Yosemite to El Capitan, and more recently, El Capitan to Sierra. Of course, when I did that, I insured that any third party applications I have were compatible with the new OS. Usually, I've had to download updates to such software (in the case of Onyx, the developer has separate versions for each Mac OS).
I will say, though, that for these last two Mac OS "upgrades", I did not do it until the "v1" (ie, OS 10.11.1, and OS 10.12.1) of the new OS came out. The reason for that is two of my critical third party applications were not immediately upgraded for "new" OS compatibility. In fact, for upgrading to Sierra, I had to wait more than 2 months after OS 10.12 came out, as TechTool Pro was not upgraded until late last month. The challenging one will be when Apple makes significant changes to their File System (ie, the Finder), and that is supposed to happen "soon", ie, sometime early next year, as an upgrade to Sierra (ie, not a new OS). It's going to be interesting (and I suspect challenging) to see what third party developers need to do with their software for it to be compatible with that "new" structure. For me, that involves at least 5 products: 1Password, SuperDuper!, Office 2016, TechTool Pro, and Onyx. There might also be some others.
I doubt that waiting for the next OS release will resolve the issues with your monitor. I have been using my monitor since February 2004, with a MacPro desktop (no adapter needed), and now my Mac Mini (needs an adapter, as you are aware), and no matter which OS, it has worked, and continues to work, fine.
In actuality, Sierra does not contain anything "vital" for my needs. Also, it looks like the critical third party software I use will still be compatible with even prior releases of the Mac OS for "some time". So, maybe sticking with El Capitan, in your case, is good enough, at least for now.