I'm not sure what your screenshot is showing. What I would expect to happen here is the remote URL gets added to the log and immediately the next item is played (I assume that is the remote URL). I would expect audio to continue if you have scheduled the 12am hour onwards.
PlayIt Live will resume automation only if tracks are scheduled after the 2 hour remote URL. Ensure the system is in Automation ON while your remote URL is playing and tracks will be scheduled after it.
Automation would that count as live assisted. because our system stays in live assisted mode 24/7?