If he uses it for PIM (calendar, task, notes, contacts) AND he syncs to PC, you might want to steer him off NIT for now. Or introduce him to GVM on the NIT...

iPhone will be getting quite a bit of boost to its PIM options soon, as the Windows Mobile , OSX and Palm favorite apps are being ported there (Pocket Informant, Agendus, Omnifocus mobile, and more) and should be available after July 11th.

In either case, if he _depends_ on PIM functions for day to day work, it may not be a bad idea to get a used machine to use for the next 1-3 months (Maybe a Palm TX or Treo) just so he can keep his grooves on while affording more time to decide for just a little extra cost.