We've had a look at this and it turns out the sceduler is behaving exactly as it was designed to. One aspect of that turns out to be used all the time by our musicians (that the loop starts on the right bar length increment, ie if you've a 4 bar loop, it waits for the next 4 bar boundary to play). The other aspect (and the the one that I suspect is causing all the trouble) is a bit bonkers on the Pico and we're going to change it to an make life easier. The scheduer actually does understand absolute song position, so when you record a loop, then stop and start the metronome (which at the moment returns the metronome to bar 1), it waits until the bar it was recorded on to start playing. This is nearly unusable (and incomprehensible, as you've discovered) in practice, so we're going to change it to behave more sensibly in a future release. We'll probably also add a 'play right now' verb so that you can kick a loop off whenever you want, ignoring the musical boundaries it was recorded on.
Our chaps use the musical boundaries to give themselves time, using the scheduler, to setup a load of loop playbacks for song transitions, like verse to chorus. If they're 4 bar loops, for example, they have 4 whole bars to key this in, which is rather more relaxed than 1 bar. Dave looked a bit horrified when we suggested making it a fixed one bar, so I think we have to find a different solution, and I think that making an instantaneous play verb is the way. We'll keep you posted as to progress with this.
John