TL;DR: Not so much "gave up" as "never tried" because I was scared away by 16GB RAM requirement.

FWIW, we've been self-hosting 2 instances (and purchase a third hosted instance), for, it looks like 8 years now, and it's had a few small bumps but hasn't been too bad. Our instances are running with 20GB of RAM, so pretty small. ~90% of updates have gone smoothly, which leaves 10% of updates that have had some sort of problem. Solutions have been found in the issue tracker in all our cases. We are a little afraid of doing updates, but do them every couple of months.

Sentry is an amazing piece of software and it is fantastic that they offer a self-hosing version, and all things considered it is a fairly easy self-host.