Niko - thanks for pointing me towards the Cowon AW1. Ordered one yesterday to experiment with and have contacted the manufacturer. It sure appears from your screenshots that the device can work in wifi Client mode, and that's half the battle. The other half is automatic posting of events to an ftp site, and for that I will just have to experiement.
I am quite familiar with the drivecam device. Great system, but lots of drivers don't like the camera pointing at them. Feels like it pushes too far into the big brother zone. Also, it is expensive and the quality of the videos I have seem is mediocre by today's standards. If I can come up with an approach that piggybacks on 'free' wifi, respects privacy, and scales to large fleets, that feels like a win.