Hey Chris, thanks for the welcome!
I completely agree with your 5 reasons to upgrade to Cubase 10. Personally I think the VariAudio update alone was worth the move from 9.5 Pro ($99). I was having a hard time using it previously workflow wise. Being that I wasn't using it enough. Now I find it much easier to get in and get out.
I have run into some funky but small bugs and the occasional crash but it looks like these may be due to third party plugins... changing sound presets in Arturia V Collection 5 & 6 sporadically crashed Cubase. Another strange one (but not crucial) is that when you click on the icon to display the version of a Waves plugin which opens a window - that window does not close... and every-time you try to close it you open a new one. So you have to restart Cubase to get rid of them.