Why is my charging handle/bolt getting stuck?

I'm wondering what is wrong with my 10/22 that the charging handle is getting stuck to where I can't load a round. When taking it apart the charging handle and bolt move fine on their own, but when I add back in the trigger housing and pins, it starts sticking again. I've tried 3 different charging handles (factory, Precision, and Kidd), completely stripped and cleaned the bolt, and cleaned everything else.

For background, this is my first 10/22. I took it to the range and it didn't cycle. After taking it apart and cleaning a bunch of factory gunk out of the bolt I was able to shoot bullets but it wouldn't cycle by itself. After about 50 rounds of manually cycling the charging handle couldn't be pulled to the rear and now I'm here. Any help is appreciated!