Okay, assuming you’re being honest, it sounds like a hardware issue. Either your RAM is corrupting, or your hard drive is prone to errors. The good news is that you have options to daily drive Linux without ending up in a situation where you have to reinstall everything from scratch.
Like I mentioned earlier, you absolutely need to be making snapshots. I'm currently running Manjiro, and I've completely borked my system like 10 times already. But when I set up my system, I made sure my main partition was BTRFS, which has allowed me to roll back easily through both the UI and in grub rescue mode.
I would also recommend that if you are going to continue to dual boot windows, make sure they're on two separate physical drives. And don't share stuff like your steam library, because windows likes to screw shit up, and steam will throw a fit if you make it read an NTFS drive on Linux.
Just don't give up, keep posting questions, and maybe even come back and post stuff like specific crash reports and system info so we can help you better. :)
If his drive is failing, and has bad sectors, windows will automatically repair damaged system files on boot. Also sounds like he's having an issue with hibernation with the window server not starting back up after suspension.