This. It’s come a long way since the early days of hosting content out of the home off Torrent Seeders, FTP Servers, and Shoutcast offerings, but support is still the biggest bugbear - both end user support, and product support of industry best practices.

Plex doesn’t automatically generate a valid certificate, for instance, even though Let’s Encrypt is a drop-in affair. Home Assistant’s own SSL support is an arcane nightmare out of the box, reminiscent of mid-2000s certificate processes. Proxies like HAProxy and NGINX can better support connection security and encryption termination, but now you have an additional layer to support and manage.

This is what I mean by “support has to improve [for self-hosting to be viable for the masses]”: if something isn’t as easy to setup in a secure manner as install, point to your content, and tie a DNS record to it, then that eliminates 99% of the potential customer base right then and there.