When it comes to most enterprise software, the term "self-hosted" is such a misnomer. It makes the exercise sound like a cool and quick DIY thing.

The reality is that most self-hosted deployments require even more hand-holding and support from the software vendor for installation, configuration, training, etc., than the corresponding "vendor-managed" or SaaS offering. This is the opposite of "self". The correct description should be "Hosting the software on infra that you own or manage yourself."

Even for many open source projects, when it seems like "self-hosting" is really easy, the easy part is running the thing on your local computer (maybe through a Docker container). If you actually self-host (meaning self-install, self-configure, self-manage, self-patch, self-upgrade, self-....) it on server(s) for non-trivial production usage, it requires specific in-house expertise, which is seldom the core competence of the teams who just want to consume this software.

Having said that, there are often legitimate reasons for "self-hosting." What are yours?