What do you anticipate to be the hardest part of supporting a self-hosted solution? I've worked a fair bit on converting SAAS -> self-hosted and always interested to hear others' pain points.

I imagine a lot of the organizations that would find this most valuable, and would be willing to pay a lot, would be the same ones that would require something like this.

I think the hardest part is the environment/support matrix, not getting it to run in the first place.

It’s usually pretty doable to make a system self-hostable on a happy path. The hard part is supporting it across lots of customer environments without being in the loop every time: custom IdPs, private networking, KMS/HSM/BYOK requirements, upgrade/migration paths, backup/restore, observability, and all the weird edge cases that only show up once other people operate it.

And yes, I think your last point is right: the customers who care most about this category are often exactly the ones who will require self-hosted.

What's your take? Curious what you found effective vs. what you deem hardest from your experience.