Hey again @benjaminfortunato Benjamin thanks for the detailed write-up. I think the fastest way to get you unblocked is a quick screenshare.
We run weekly office hours where you can walk us through your app live. You can sign up here: Come join Retool Office Hours (now in Zoom)! We'll be able to tell you on the spot which items are existing limitations, which look like bugs worth filing, and which have workarounds you can use today.
If office hours doesn't work for your schedule, reply with a short screen recording of whichever of the four is most blocking, plus a link to the app, and I'll dig in from there. 