I just got one of these:
http://store.yahoo.com/justdeals/hp.html
I'm surprised by how much I like it. Big beautiful screen, long battery life, reletively fast (for Windows CE). And dirt cheap. Kinda hard to find software, but the stuff I've found works well. I got NetHack, Gnuplot, and a book reader on there now. MS's dev kit is free. Haven't found a Palm emulator yet, or a good free Gameboy emulator.
I think it might even do what you need. ActiveSync (you'll need the latest from MS) creates a named "partnership" with each PDA you plug in. So I know one desktop can track two PDAs, but I don't know how well it works. Guy I work with is getting one too, so I might be convinced to try it.