I have the unfortunate experience of supporting a rather large application in a rather large bank. This application is on a pair of load-shared Windows Terminal Servers 2003. We've been fighting problems with trying to get SIMPLE PRINTING to work for the entire time. If printing is your big issue, I don't see how moving to WTS is going to help you at all.
If anyone can prove me wrong and that it's just some sort of configuration issue, PLEASE LET ME KNOW! If you can make it work for us, I'll be overjoyed and send you something nice. (I mean it--if you can solve my biggest pain in the tookas, I'll find something nice and send it to you!)
Our specific printing problems are (1) The application and/or WTS gets confused and spits out partial printouts (yep, we're using WTS-approved printer drivers!) (2) The print spooler(s) periodically hang for no good reason (3) There's a "ring of pain" where OPS points to the network, the networking support points to the application team, the application team doesn't have permissions to look at anything to find any answers...
Uh, sorry, I didn't mean to start off on a rant. Let me just say: If I could remove any one application from our site. It would be THAT one.
I think the problem is mostly that it's frequent enough to be EXTREMELY frustrating, yet rare enough to be impossible to reproduce on demand, and there are enough parties involved that you can never get enough brains focused on the problem long enough to get the damn thing fixed!
I wish you better luck than I have had so far...