One of my relatives has a son interested in game design. Though I’m not much involved, I’ve watched it enough to be able to give something of an answer:
Unfortunately, the company doesn’t do many games anymore; those we have been done were coin-operated, and often redemption (tickets; chuck-e-cheese type stuff)
I presume by the involvement of software that you are referring to computer/video games. (I’ve also dabbled in board games, but very few people are able to make a career of it) I’ve watched the industry a bit at times, but never really been involved in it. What aspect is interested in? There is programming, art, sound, production, and even ‘design’ is specializing into story/writing and mechanics (possible called ‘game design’) Aiming smaller at the casual/web/downloadable market might be an environment were multiple talents would be more common. Things may have completely changed by the time he’s making a living on it, but that could be a place to start now.
There are a few game development schools – just don’t confuse development with design. Develop is the whole thing (programming/art/etc.) and very often their brand of ‘design’ is write up a design document and then a bunch of people go build that, whether or not it’s good. Mostly I speculate; I’ve no personal experience and they may have much brighter people than I give them credit for – just make sure they are offering what you want if looking in that direction.
Otherwise, the question of schools comes back to the area he is interested in. For true game design (which I should mention is a touch gig to get) liberal arts may actually be the best bet. See the book Rules of Play (below) for an idea of the breadth required.
I haven’t looked into tools lately. I ran across Squeak EToys recently; it’s designed as a first introduction to programming in an interactive environment. Beyond that, I’d recommend finding a game framework for a dynamic language such as Python or Ruby; I also believe there is a DarkBasic that is focused on games.
http://www.gamasutra.com – web site tied in with a publish of game industry magazines and such (you could also subscribe to Game Developer magazine I suppose) News, articles on various topics in design, programming, and trends.
http://www.myhq.com/public/r/a/rauros/#104300261935570145 – my game design bookmarks; some are related to board games or weird abstract things about the ‘meaning’ of games and suchlike.
A Theory of Fun (Raph Koster) – fairly light essay on fun; illustrated.
Rules of Play (Katie Salen/Eric ZImmerman) – a textbook of game design, but in a broad sense – includes board and playground games in addition to computer.
Patterns in Game Design (Staffan Bjork/Jussi Holopainen) – more focused on computer games, but a little dry and perhaps not the best starter book.
Chris Crawford has written a couple of books; I believe The Art of Computer Game Design is available for free online, along with a lot of other writings. Just be aware, with respect to breaking into ‘The Industry’, Chris checked out of it a while ago, and many of his writings refer to a bygone age. http://www.erasmatazz.com/