@doobu @Aidin
Basically, I just kept making another ticket if 24 hours or so had passed since the response on the last one. I know that Squarespace doesn't like this, but I kept asking for updates within my first ticket for like 5 days, and was receiving no response. Felt like I was basically playing "support roulette" until I got somebody who knew what they were doing. Be as detailed as possible, I'd even recommend sending Loom recordings of trying to re-enable the autobill and showing it fail, things like that. Just to pre-emptively rule out any unhelpful responses like "here's a support article on how to turn on autobill...". I would also include links to threads like this one to help demonstrate how widespread this issue is. I will also say that the issue was fixed rather quickly once I mentioned that I would be looking into transferring the 30+ Squarespace domains I manage to a different platform if this couldn't be fixed...
I wish I could give you guys something more helpful than that, it really does seem like it's luck of the draw at this point. Just be persistent and detailed. If I learn anything more about anything we can do to solve this issue on our end I'll make an update, but no luck with that so far.