You're going to be kind of stuck with most models out of the box. There were some early WinCE devices that had qwerty keyboards built in, but battery life was horrid. Most PDA's have the ability to add on one of those foldable keyboards now, so if that would satisfy him, you could look for one (keep in mind it adds $100ish to the price). For what he wants to do, I'd go with an IPAQ or any of the new pocket pc's. As long as they have CF compatibility, there are modems available for them.