If you are sharing PCs with other people, make sure to login using separate Windows accounts.
Always use a secure password, maintain antivirus software, I recommend Avast. And encrypt the data on your hard drive.
Are you sure that your USB cable is still in good and working condition? Are there any drivers that you need to install for your PC to recognize your phone?
I don't see why anyone would ever regret making an "upgrade".
Upgrades are designed to be better than their predecessor therefore there are many improvements that can enhance the user experience.
This is like asking whether somebody regrets trading a 1995 SUV for a brand new one.
Revert back to Windows 8.1 and try the upgrade again, if the problem persists, you can either find a way to fix the problem or stick with your current Windows.
More RAM can help if you're using a lot of high resource applications at once, if not, then don't worry about it. And if you ever need more RAM, be assured that the option to upgrade is available.
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