Plex SERVER Auto-start - How?

Fair enough. I re-tested on Windows 10 Pro and it still works there as well (PMS not available after restart with it disabled; PMS is available after restart with it enabled without logging in). Microsoft mentions a couple of things in the article I linked originally which could cause this to fail, so perhaps that’s a contributing factor.

Given this, it may be that your only solution will be to run PMS as a service.

There’s also this ancient, not very popular (by votes) feature suggestion to natively support running as a service under Windows.