I've finally beaten radio into submission and have it uploading to my domain.
It uploads in batches of 25 files and for some reason was stalling and taking forever. After tweaking stuff to try to take care of the staling problem it looks like it might be working now...
In the end I ended up debugging through the very strange scripting language that they use. It is a wacky mix between a really primitive intentional programming (with the outlining) and pascal. The environment for editing and debugging this stuff just seems arcane. This just screams for .Net....
.Net killed the Radio star..