Jim says that every time he does a Windows update, something goes wrong. It always deletes the restore point after updating, too. Leo says that Windows is deleting the restore point because he doesn't have room for a second one. Freeing up space on the drive could help. Leo doesn't trust restore points though, anyway. They don't work very well.
The bigger issue is that Jim has something that breaks during every update. Leo suggests that he back up his data and start over with a fresh install by pressing Windows Key and typing Reset. He can then reset without deleting data or reset and start over with a clean install. Leo suggests starting over with a clean install. This will not only get it back to running like the day he first bought it, but it will free up a ton of space from unused programs and temp files that he doesn't really know he has in his cache.