Damn, I thought I could outsmart this sync bug by putting my miniSD card into my old Audiovox SMT56000 (running Smartphone 2003 instead of Windows Mobile 5.0), syncing all my WMDRM'd content to it, then swaping the memory card back into the SDA. I guess it was stupid of me to think that Windows Media DRM wouldn't prevent that, but hey... I had to give it a shot.
The interesting thing I've now noticed is that if I keep syncing, I seem to be building a collecting of more than 25 tracks. I don't know if the "bug" is just limiting it to 25 protected tracks *per* sync, or what. But at least now I've got a few dozen tracks on there. Someone at work actually suggested that this may not be a "bug", but a way for Microsoft to appease the carriers (for those that have aspirations to sell over-the-air downloads for a couple bucks a pop). It actually rings true to me, and is a frightening thought reminiscent of the Motorola Rokr and it's artificial 100 song sync limit. Scary.
Let's just hope T-Mobile doesn't have aspirations to be a music service provider, and releases the OS update soon... I can't rely on guaranteed Edge data rates that just allow me to stream everywhere I go.