I can usually help people out for $100-300 when they get in the weeds with self-hosting. Self-hosting also allows you to use plugins that would require moving to discourse.org’s Enterprise plan. I have done installs for several hundred self-hosters and though I do command-line upgrades for some of them, a whole bunch of them just keep going for more than a year before they need my help again.
I can also keep offsite backups and monitor your site and provide regular upgrades (Discourse Server Maintenance – Literate Computing, LLC).