Answers to the qu-est-ion-ez....

Robert- Hello... Doctor.... awh yes. As far as the recording programs, well...we ripped Cakewalk for free but it usually costs. Audacity is free. Garage band comes free with any modern Apple computer, and Pro Tools is expensive but worth it.

Nick- well pro-tools is quite spiffy, thats all i can say about that. if you want an affordable guitar, get a squire pack, it comes with a practice amp and all of that good stuff. or an epiphone pack which is about the same, just different styles of guitar, pretty much.

Matt- Well, If he is just going to start out then i would recoment don't getting any kind of pedals at all to begin with. If we wants an amp to be able to use different effects like mine, then he could get the spider three line 6 amp thats only 15watts with 1 10" speaker in it. It's small and does the same thing mine does, mine just is bigger with more power. This amp will run you about 100 to 150 depending on where you go and if your able to talk them down a bit.

Now, for guitars. You could do as nick suggested and get one of the starter packs. I would recomend the squire pack because if you wanted to upgrade your guitar later but do not have the funds to do so, you can switch out the pick-ups out and get new better ones for cheaper and it will make the guitar sound much different and better. Those packs can run you from 200-350 dollars. But, if you wanted to just get a guitar and an amp then i would suggest Ibanez guitars. They are very good quality for a good price. The only problem with Ibanez is that many of them have a Floyd Rose on them or have a lockable nut at the top of the neck, making it hard to tune. The other options i would suggest is Schecter guitar. They can range from 250 to 2000 dollars. It all depends on what you want in a guitar.

Find out what kind of music he wants to play also;
Metal:
LTD/ESP
Schecter
Les Paul Epiphone
Ibanez

Classic Rock:
Telecasters(fender)
Strats (fender)
Gibson

Rock:
Almost any kind, depends more on style and what kind of amp your using for the situation.

If you want more of a classic rock sound for amps
THen go with a tube amp, they generally are much more expensive since most amps these days are digital or electronically enhanced.