I didn't say anything about private vs public data. I commented that you trust Google, but not MS/Windows.
To respond to your points:
1. Old hardware/software not being supported is nothing new. That's been happening all along.
2. There should be no updates interrupting your work or resulting in a blank desktop - you may well have to configure settings and disable updates if that is an issue for you.
3. What reason do you have to suspect your settings would not stay put? Any why do you trust Windows less than.....well, any other device/service? Cellphone? Games console? Tablet?
For a ridiculous comparison, it'll maintain your settings better than a stove will maintain the clock settings after losing power.
4. Again, nothing much has changed here. OS's have always been updating. Things have changed a little as to how they're implemented, but historically support would simply cease.
5. The 'upgrade' may uninstall/change/mess with a driver/program/file.....afterwards, again, it's no worse now than it's ever been.
6. No, your data is not being uploaded/downloaded (at least nothing non-OS related).
7. If you don't disable it, then it's a possibility.
8. Again, can be disabled.
9. Their feedback messages have a lot of paranoia about them, absolutely. You never hear the 'good' reviews, much like a restaurant feedback on Yelp or similar. Bad experience (or perception) and people will shout it from the rooftops. Good experience/perception, and nobody hears anything.
The unknown aspect of what's happening with your images. Do you use a cellphone? Android? Apple? etc. Why would you be convinced they're leaving your files alone either?
99% of your issues seem to be either misinformation, not being prepared to safeguard your own privacy (as much as you can while still using a corporate entities software), or outright paranoia. You're comfortable with Google, but not with Windows - that's a complete double-standard which I still can't wrap my head around.