Cactus Music
Overall the best reason to keep abreast and fully updated is the support and functionality. You fall behind and your on your own.
I went from Windows 7 to Windows 10 (didn't like Windows 8) and Windows 10 is snappier. Another difference is that Windows 10 is multi-client with respect to MIDI. This is a major improvement if you, for example, use a synth editor with MIDI and want it open while SONAR is running. From a UI standpoint, I do like the way W10 integrates W8's ill-fated tiles.
My gripe with upgrading is it takes time away from recording to muck about and then re learn how to do something. I feel like I could never fully grasp Sonar right now.
You actually don't need to...a quick story. I've been using Live for live performance since it was introduced. At one point there was a major update, and having helped write the manual for Live 2, I was able to have it updated for free. I later ran into Gerhard Behles from Ableton at Messe, and he asked how I liked all the new features. I was embarrassed to say that I didn't use 90% of the new features, that what I had been using was really all I needed. I thought that perhaps he'd be a little offended, but he was actually delighted. He said that's as it should be - a program should have enough features that different people can use it in different ways.
SONAR is my DAW because I
need to do so many different types of projects that I do end up using just about all its features. But if I never had to do a particular type of project any more in the future, there would probably be some features I'd never use again.
I understand "if it ain't broke, don't fix it" which is why I stayed on W7 for as long as I could. But I also understand "if fixing it don't break it, go ahead." I updated to Windows 10 in order to stay current and review/test software in that environment, but ultimately found it didn't break anything (except for the V-Studio drivers - it's a hassle to get working under Windows 10), and the somewhat better performance - as well as multi-client MIDI - was welcome.