I use the Boomerang looper for live shows. I'm not very familiar with the JamMan functions and features.
I do have some tips though in general for using a looping pedal.
1) As far as timing, work with a metronome. Tap your foot to the beat and when it's time to press the pedal just shift your foot over.
2) When looping, make it part of the composition. Don't always just stack parts. Maybe stack a couple parts, then solo over it, then stack another, then solo again. Or drop the loop and go solo guitar for part of the song and then go back to the loop. Try some variety of what parts you stack. Start with the bass, then add the percussion, then the accompaniment. On another piece start with the percussion, etc.
3) The ending is the hardest part in my opinion because you build up this big loop and you have to drop it somehow. There are multiple ways of ending a loop though and I would try to vary your endings. It could be a sharp snappy ending that is part of the loop. If you have an undo function you could drop parts. If you have a volume pedal you could fade the loop. Some pieces I drop the loop and immediately go solo to finish the piece.
4) Don't use your loop pedal too much in a performance. It can be very pleasing to an audience but if you use it too much it just gets old. For me I typically don't use my pedal more than 25% of the time in a gig. I try to do it even less and also I don't do back to back looping pieces.
If you want some examples for looping I have a few looping pieces on my recent album release called "ALIVE". I'm not sure if I'm allowed to post my website on this forum (I'm a newbie), but if you search David Youngman Guitar in Google you will find my website. The looping pieces on the album are "Starry Night", "Oh Susanna", and "Jesus Loves Me".
Hope this gives you some ideas.
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