Owning things ties you down.
True, but it also creates an implied bond between you and the manufacturer. Or at least it used to. Without that bond there's even less obligation for things to work properly.
As to your other point, I feel we can be pretty confident that sometime in the next four years US corporations will see a decrease in regs and/or in their enforcement, and possibly lower taxes as well. When that happens will finance departments let the pressure off? Personally I see the existing pressure coming more from big-finance, high-frequency trades and large asset funds that relentlessly seek to maximize profits which come from relentless cost-cutting of any kind, whether it be from lowered taxes, decreased investment, accounting gimmicks, m&a or what have you. At least in terms of Apple, their current effective tax rate is not particularly high in the corporate world but considering their assets, revenue and market cap it's true that even marginal savings for them amount to a huge heap of money, hence the whole Ireland thing. In any event the philosophical shift in the role of government will in the coming years make for an interesting experiment in political economy.
The subscription model for the OS and major apps, the constant updates, the cryptic error messages, the Metro-style UI that should never be on a non-touch device (but is), the ads and tracking, the slowness and unreliability of OneDrive (compared to Dropbox, iCloud, Google Drive), and so on.
I missed that before. Most of which I agree with but I do want to stick up for OneDrive a bit. I have the Office version and it's been nothing but rock solid for me. Unless you mean "unreliable" in terms of its morphing feature set, e.g. is MS going to suddenly change the amount of space they offer the user or if placeholders ("on demand sync") will work or not work this week.
Changing subjects a bit may I gripe about how every site these days seems to think I want autostart video with sound. At least they used to limit it to their desktop versions but now my phone is downloading full-length infomercials it seems. Oh and that modal "sign up to receive our email" pop-up that still pops up even after I've already signed up to receive your god damned email. I could write a book or at least a very long Usenet post about how the web has totally gone to seed compared to the days when we actually used to call it the World Wide Web. Get off my LAN, you punks!
EDIT: About your dad, after her husband died, my aunt recently went from owning a house to, for the first time in 30? years renting an apartment. She said she didn't want to have to be tied down with shoveling show in the winter, other maintenance and routine repair issues, market conditions if she wanted to quickly move, kids moving back in, etc. She feels free and unburdened. At the same time, my mother decided to go from renting to owning an apartment, and it's been nothing but headaches, so many unexpected expenses, insurance issues, etc. Ownership is not for everyone. If I recall correctly you mentioned that you tend to obsessively maintain things in just-like-new condition. With a home, especially if in a floodplain and with a wide seasonal temperature swing, that means being stressed out all of the time.