Some comments from rec.skydiving:
Your spot would have to be accurate to within inches, wouldn't it? At that speed, at that height, a couple of inches either way and you could be up creek without a paddle!
wouldnt you have more altitue to track to your destination? how far do you think you could get (and how much freefall time) with a birdman suit?
To say nothing of being late for work! It would be a fun commute, however.
Flat spins could prove interesting when one considers the law of conservation of angular momentum :-)
A birdman suit while de-orbiting from 300,000 feet? Not *very * cool* at all...
No doubt you have little space shuttle heat tiles glued on the birdman wings to keep from burning up, right?
Shoot, if the glue and the fabric hold up, ya might make it down to 150,000 before you began to look like a small version of the MIR space station over the South Pacific.
It would lend a *whole* new meaning to the phrase Smoke'n it down.... :-)