We were on various 'bought' versions via 'work' discounts, but with new machines, had to migrate to 365. I fortunately get it free, and we have the Adobe suite of stuff on my daughter's machine for free (art stuff). But, with 365 I have to make sure the software is logged onto my 'account' although not physically connected to the work one-drive (only our paid personal one). Down side is it can ask for authentication randomly - great if I'm at home, not so good if daughter can't access it (she should have it with college). We've got secondary phone authentication too now that makes the process a little easier, but not when you've changed your phone - had to get it all reset.
I prefer 2016 etc to 365 - menus less 'fancy' and more utilitarian (i.e. user friendly)