I don't think Sentry is being evil or is trying to make it harder to self host, but I do think that Sentry doesn't have a big incentive to spend a lot of effort making it easier to self host. Again, I don't think that's evil. I think it's entirely reasonable and ok, even if it does make life harder for some people.

Maybe this virtualized system will make things easier. If so, that's great. But if it ends up not working out, or if it does, but over the longer term things get more difficult again, I think that's still just kinda how things happen sometimes, and that's ok.

One of Sentry's goals is for Sentry themselves to operate it as a hosted cloud service. Architecture decisions made to further that goal can naturally and reasonably be at odds with another goal to make it simpler to self host. Sometimes things can't be one-size-fits-all.

I already mentioned this elsewhere here but Sentry does have an incentive to improve this. That’s because the complexity creates challenges in the operation of smaller instances and during development.