My second run with Apple Watch was better. Not just the run itself, but using the Watch while running was a lot smoother.
In my first run with the Watch, I lost audio when my Airpods appeared to have died midway through and each runkeeper pace announcement via Siri would stop music. This time my Airpods made it easily, but my music still paused every 5 minutes.
I believe the issue with my Airpods in my first run wasn’t my Airpods, but rather the podcast I was listening to was only partially buffered from iPhone. By my second run, Overcast and my watch have had plenty of time to sync and plenty of audio for my run.
The pausing audio issue I believe to be a bug with runkeeper. To test this, for my next run I am going to try running with just the Apple Workout or Nike Run Club app and see if audio resumes after callouts. If it doesn’t, then there’s potential that it’s an Overcast bug, and I’ll need to try with the stock Music app (and sync some music I’d like to run to!).