Xbox 360 download / purchase history issues

I'm unable to redownload hundreds of games I bought over the years, I recently had an issue with my Xbox One that stopped working randomly (out of warranty unfortunately), so I pulled my 360 out of the closet knowing I had hundreds of games I had purchased
over the past decade for it and many I never got around to playing, going back from the XB1 to 360 interface is a difficult transition but my XB1 was having issues and was slowing down anyways so it wasn't too bad. I got into my download history but when going
to the bottom of the list I just get an error message every time, it spins for about a minute then I get an error and that happens every time. So I went online remembering that I thought I recalled being able to just download things from my purchase history
/ download history to my 360 directly from the website, but there seems to be no option? What gives? I'm broke right now and can't afford a new console, and this is really irritating me to not just be able to access the majority of my games that I purchased.
I had a feeling this digital stuff would end up being a nightmare some day but not this soon, are we finally seeing the real effects of the digital gaming era? If this is the case, I will never purchase digital again and may even leave the Microsoft/Xbox ecosystem
entirely because it's been nothing but various issues that I've pushed through over the years.

:)