Can you educate me on what is involved in having music transcribed?
This isn't something I actually have a lot of experience with but I don't think it's something you'll need to worry about with modern keyboards, they will all support MIDI output which is how you send the information about the notes from the keyboard to a computer program. They'll all also support sending the sound itself out as well so you could record to a device or send to an amp, etc. Just like computers with different input/output ports, it's possible you'll need a special cable or converter box between the keyboard and the computer (or even ipad) but that really depends on which keyboard and which computer and probably won't be very expensive. I think focusing on feel/weight/sound quality are the right things and agree with KpbS that the musician dept might have some good recs (and maybe even discounts, who knows).
What software do we need to be able to have it transcribe music?
There's a lot of different options here, from free to very expensive professional versions (with student licenses) and if he takes any sort of composition or arranging classes my guess is they will likely have a program they want to use.
~ Dawn
Our little monkey (4/2011) & his early holiday present 12/12