Various issues with Plex's basic playback controls (play, pause, next, previous)

I have had the same issue with bluetooth controls since 7.28. (started with 7.28, was not a problem at all with 7.27)
I have the same/similar problems as you, mainly with pause/resuming not functioning properly on bluetooth device connect or disconnect (my car, like yours).

Been trying to get support on this in this thread where it was reported in a 7.28 beta

As well as in a thread I started here:

I sent my logs to @marekszulik who is aware of the issue but has had trouble reproducing it. Maybe your logs would be helpful as well. (?)