I see now that if I turn on my 450 with chirp searching already enabled, it will pick up the chirp right away. If I have chirp searching off, attempt to send/receive waypoints from another gps, which fails, then it will never pick up the chirp after enabling chirp searching unless I power cycle the unit.
So to sum it up, chirp searching works unless you have a failed attempt at wireless transfer, you will need to power cycle, it seems to crash the wireless radio.
Well, I hade the same problems, downgrade my Oregon 450 back to 4.20