Hi Chris!
I just did a quick check on your input. A symbol lights up whenever an IR command is actually sent, so i tested the play and other buttons in both activity and device mode. In device mode it lights up and flirc recieves it, but in activity mode these buttons show no activity. So it seems to be more of a misconfiguration on my part or some software error on logitech's part. I'm guessing it's number one, so i'll wipe it and start over again. I'll post my findings here, should anyone ever google this and have the same issue.
Flirc in itself is an amazing simple product, does as described and does it well, i'm very happy with that.