Electric or Acoustic? and how much are you looking to spend?
 The best guitars run into the 1000's of dollars, but you can get pretty good beginner setups for around $100 or less, if you check pawn shops you may be able to find something of good quality for a fair price.

 The biggest problem I have always noticed with cheap guitars is the strings being like 1/2 inch off the neck, you definetly want to avoid this! The strings should be close to the neck and there should be no buzzing when you press the strings down at any fret. This can be adjusted to a certain extent, but you kinda need to know what your doing or you can throw the whole thing out of whack.

 Wal-mart sells beginner setups for fairly cheap, but I'm not sure of the quality, you might want to stop into a music store and look around and talk to someone there.

 Pippen, being from the Chicago area, I would suggest checking out a Guitar Center, here are some locations:

Guitar Center Chicago
2633 North Halsted
Chicago, IL 60614
Store Hours:
M-F: 10-9, Sat: 10-7, Sun: 11-6
Phone: 773-248 2808

Guitar Center Arlington Heights
2375 S. Arlington Heights Rd.
Arlington Heights, IL 60005
Store Hours:
M-F: 10-9, Sat: 10-7, Sun: 11-6
Phone: 847-439-4600

Guitar Center Burbank
8250 S. Cicero
Burbank, IL 60459
Store Hours:
M-F: 10-9, Sat: 10-7, Sun: 11-6
Phone: 708-422-1400

Guitar Center Highland Park
143 South Skokie Valley Road
Highland Park, IL 60035
Store Hours:
M-Th: 11-8, Fri: 11-9, Sat: 10-7, Sun: 11-6
Phone: 847-579-1830

Guitar Center Villa Park
298 W. Roosevelt Rd.
Villa Park, IL 60181
Store Hours:
M-F: 10-9, Sat: 10-7, Sun: 11-6
Phone: 630-832-2800

 Guitar Centers are huge and have awesome selections in all price ranges, I'm sure you can get the advice you need and find what you are looking for there.

Enjoy!

 Lessons can be quite expensive, they will probably run $20-30 per hour or in some cases per half hour.
 
 If your boy picks up quickly on things, he could teach himself quite easily, there are plenty of books that show all the basic stuff.
 If he is mainly interested in Country music, that makes it even easier, just pick up some tablature of his favorite songs and he can learn to play along with the CD or tape, country music is very simple and pretty much built on simple chord combinations, probably not a bad place to start learning, I'm not big on country music but it will teach him all the basic chords and it's easy to keep time with, it's when you get into the speed metal or Classical genre that things get REEAALL tricky.

 When you go to the guitar center, I'm sure they can point you in the right direction as far as beginners kits, usually they come with a book to get you started, some picks, a strap, and a stupid pitch pipe to tune the guitar with, word of advice..get him a real tuner, you can get a good one for 20 bucks, and nothing sounds better than a finely tuned guitar, I have a great sense of tone, I can tune by ear without a tuner, but I still use one because then you know you're dead on, and you can tell when you start playing chords if a string is a little out.

 Once he learns a few chords and how to put little riffs together, he'll be writing songs in no time, at least that's what happened to me.
I don't really play much anymore, but for about 20 years from age 13 or 14 up until just a couple of years ago, I lived to play and write music, I still break out the acoustic now and then, I have a beautiful ovation that plays sooo nice, it's the purple one that is in the picture over in the instruments thread.

 Certainly if the cost doesn't matter, a few lessons would push him along a lot quicker, but I always believed that teaching yourself to play is what creates a musicians own unique style, I'm sure guitar center gives lessons, or look on their bulletin board, you might find someone that gives lessons cheaper and could be more of a mentor, instead of the assembly line that a busy place like guitar centers lessons would probably be (I don't know that that is the case.)

 You are on the right track Pip, just go to guitar center and talk to someone there about all this stuff, most guys who work in those places are musicians themselves and are more than happy to get someone new started in music.

 Keep me posted on how things go.

   

  I have never owned an Alvarez myself, but I know they make a good quality instrument and they have a good name in the industry, a lot of top performers use Alvarez products, the price seems reasonable too.
  I became addicted to Ovations somewhere down the line and I still own 3 of them, a 6 string acoustic, a 12 string elec/acoustic, and my pride, the purple 6 string elec/acoustic.
  Ovations are awesome if you like the sound of a roundback guitar. As with anything else, prices vary on which model you go with.

Ok, I went to the Guitar Center tonight and narrowed it down to three choices, all of which were $199.00

a Fender 095-1101

a Takamine G230

and a used Ovation CC/67

Anyone know these?  Apparently the Ovation is made by a company called Celebrity?  They are all accoustic and the Fender and the Ovation both have electrical pickups just in case.

I'm going to put one on layaway tomorrow or the next day...

With the stand, case, and tuner, it'll al come to around $250.00

There was actually this enormously fat Hisapnic guy there (I could have sworn he was that guy from Blues Traveler) and he helped me out in that department.  I'm no judge of guitar players, but this guy seemed very good to me.  He didn't even work there.  And since my first rule in life is 'Never trust anyone who is trying to sell you something' after the salesman gave me the lowdown on several guitars and what to look for, I went back and talked to this guy.  I think I'm going to go for the Ovation as it's in great shape and is a way to get him a better guitar for less money...

Well, I did it.  I put the Ovation on layaway.  After we took the guitar to the counter I noticed several of what looked liked cracks in the enamel of the finish.  I ask the salesman about them and he said the previous owner had probably exposed the guitar to sudden  temperature changes (as in leaving it in the car in the winter) or too much humidity.  He assured me it wouldn't affect the quality of play, and I decided not to worry about it.

  Good choice going with the Ovation, I think Ovations are one of the best sounding Acoustic guitars out there, all the guitars you were looking at were from good companies that make excellent quality instruments, but you just can't go wrong with an Ovation.

  Here's my collection:



  My purple Ovation in it's blue plush case: