Wow dcrowell you've lost a lot of stuff, your route must be treacherous.
I've lost one of my PB superflashes 3 times (half of it anyway) for various reasons, I went back and found it a day or more later only because I had an idea of where it came off, usually a crash site... That thing must have nine lives.
Pannier fell off once on a curb hop, it was 100% my fault for not fully securing it properly to the rack. My Macbook Air took it like a champ.