This is a common problem. I also have a severe dislike of the Tesla updating process. I have the feeling that it's made for people who have a garage with 24/7 wifi. Without that, you're out of luck. In Okt and Dec of last year I have spent 4 hours per month on updating. This is with a 2020 Model 3.
The solution by the way for this problem is probably to go into the service mode and reinstall the software [1]. It will give some nasty warnings but it should work. I tested it myself once and for me it worked.
Another note:
> But this is Tesla, and it seems like no one is behind the wheel.
Yes that's true. It's very hard to get support and I also have some gripes about how some serious problems are not fixed. Tesla does have amazing online manuals though so that does alleviate the situation a bit. Also, if I need service I learned it's best to just walk into the service centre and ask there. They are very reasonable then. Just don't try any digital way. There is no point.
[1]: https://www.reddit.com/r/TeslaLounge/comments/x00cbj/comment...