Personally I'm more worried about Windows 10 updates breaking my UAD-1 or MidiMan 2496 drivers than I am about one of them breaking Sonar. The last Sonar/Windows 10 Update that I remember was with some VSTs and not the main Sonar program. I remember a Beta update for some of the plugins, but personally I am not really sure what fixed this as it did not impact everyone and I don't remember the fixes going live.
This puts into context my earlier comment about keeping other software components the same as well as Sonar. One of my biggest concerns is keeping my legacy hardware working. As long as it does there is no point getting anything new but when/if the drivers finally fail I'll buy some new devices at which point I would personally prefer to be on supported software. So my first concern is around hardware and driver support, legacy for Windows and new for Sonar.
Second point is that I think I have everything that I need now so theoretically I won't be buying a lot of VST effects or instruments which would be good for sticking with Sonar. But plans change quickly as mine did on Friday when I got the Korg email and decided that adding the Odyssey to my Legacy Collection would be great given that its not part of Syntronik. Good news is that it works with Sonar but what if it did not, who could I get to fix it? So new or upgraded VSTs would be my second concern if I stuck with Sonar.
What swung it for me in the end was cost. The Cubase crossgrade is not cheap but I'm on a qualifying version and I'm not expecting to see a better offer in 12 to 24 months. For me it made sense to switch now, taking up the Steinberg offer rather than wait.
Having made the choice I'm finding Cubase has a lot of good points although I agree that some things are not very intuitive (for someone used to Sonar). Support of external MIDI Modules is really good and although its a pain having to go through the steps required to get my modules setup I have found a few things that will make things easier that as far as I know are not possible in Sonar.
I think sticking with Sonar is really a very personal choice and depends on a lot of factors like; is this a good time to change, can you afford to change, how scared are you by Windows 10 updates (you should qualify this by asking why you are scared of them), is your workflow tied to Sonar, how long are you prepared to wait to see if a Sonar Phoenix emerges, etc.
Not forgetting that you could actually use two or more DAWs so keep Sonar, buy another and use them in parallel until you are happy with the new one or Sonar dies (which could be 10 years or more based on how long some software has survived Windows upgrades).
I would say though that if the only reason that you have for going through the pain and expense of switching to another DAW right now is a fear of a future Windows update then that's probably not the best reason that I can think of.