Fred, how many years of playing does your boy have under his belt? If he's totally new, get him a $300 used MIM Strat. They are a huge value for the money, play and sound great and you can get your money back out of it, if your son doesn't stick with it. I have a lot of guitars and more amps, but the best ones are the ones that make me want to play all the time, the ones that make me think about them when I'm away from the house. The best way to ensure he practices and sticks with it is to get an entry-level, but playable guitar on which he can play the kind of music he likes. Getting my grandfather's ancient Stella acoustic and learning Love Me Tender and Proud Mary when it was the first VH album that made me want to start playing was not a recipe for success.
Here's a beater partscaster I slapped together from spare parts laying around. I have the pickup coil split, so I can get a nice Strat sound from it. But it also has the VH superstrat vibe and can handle that stuff in spades.
