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maybe since he moves around a lot you could get him a nice backpack or something to keep his stuff in. You could even get him the back pack and load it up with some of the other things mentioned previously. You are doing a great thing just by being his mentor.
Get a picture of the two of you together, one for you and one for him. I have one from when I was a mentor in High School, and it is one of the few things I still keep around from those days.
 
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Go with the Game Boy. It will cost you a little more than you may want to spend, but would probably mean more to him than you will ever realize.
I don't know if a Gameboy or ipod are a good way to go since they cost money for new games and music to use them. If he is poor there is little chance that he will be able to get new games for a gameboy, and might not be able to get replacement batteries to run it.
I like the bike idea if that's something he could get use out of and take with him. You can get a decent bike at Wal-mart for well under $100. A bike is big so it might be hard to take with him next time he has to move.
I liked to read at that age, but I can't speak for this kid. I think I also got a slingshot (a weapon might not be a good idea) around that age, and that is fun to play with and practice shooting at things.
A baseball glove would also be a good gift from you. You might be able to get him interested in baseball and playing catch is a good way to bond or relieve stress. My little brother and I used to play catch all the time.

-edit damn too late. Forget what I said I'm sure he'll love the Gameboy
 
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