I had to jerry-rig several XP software programs to get them to work with Win7. I have not found any comparable Win7 programs, so I have to stick with the old XP ones.
I already know that IE 10 and above kills by IE-based tabbed browser and productivity add-ons.
I also lost a laser printer when I went from XP to Win7, because there was not driver for the 64-bit Win7.
Unless there is something spectacular in Win9, I foresee no reason to upgrade.
Pale Moon runs circles around IE 11 in terms of reliability, ease of use, and especially by allowing stable browsing opening new windows rather than the wretched TABs. IE 11 has frequent {at least once a night} crashes with TABs also just not quite as much as when you are browsing with windows instead.
Another biggie in the W/8 annoyance dept. With W/8/8.1 IE 11 browser and other MS products like word pad I kept having a type over issue when I would want to correct something. Nothing is more frustrating than to be typing something and realize each keystroke is erasing your work by the program typing over it. Oddly enough the issue got resolved in XP but came back in W/8 with IE 11. These type of issues MS ignores also. For that reason Pale Moon is my browser and LibreOffice my writer. Yes Pale Moon and LibreOffice did it right and IMO MS gets a huge fail.
MS bring back a Mail Client that handles multiple e-mail accounts and include it in the package. Your APPS idea for home/business computers is a rip off. The reason a person buys a computer is to have these functions in the machines OS to start with. MS is starting to act like Mr. Haney in Green Acres.
Make Opting out of Cloud features easier to find and do. Some users do have limited monthly allowed usage and having the machine Chat with Corp is not desired. Again most persons buy a computer to back up and store on their own.