I tested this and Guaillaume's information is probably correct. There seems to be a time out involved where if I tried to connect with playing media too soon it won't play but if I give it at least 10 minutes then I can connect while playing something.

For now, I put in a bluetooth dongle and I am able to play through bluetooth, stop, and reconnect with no issue. I'd rather use airplay but this will work till you guys come out with your airplay2 implementation.

Thanks