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I've been down the same road twice, George. When it comes to teenage boys and playing guitar, many are called but few are chosen. Your wait and see approach is best in my opinion. The more he invests himself, the more you can invest. But you need to make him work for it. If and when he demonstrates a genuine commitment, you can then up the ante. Meanwhile, somewhere in the coming year, you can see to it that he becomes aware of a goal. There are many players on this site who can tell you about subtleties like tone and action that make the difference between entry level and better guitars.I know very little about guitars myself but then again, this confession may be redundant due to my comments in the previous paragraph.You seem like a great Dad.
I'd love to sell you the guitar and amp I bought for my son five years ago, but despite the fact he doesn't play it, he likes it as a decoration in his room. Maybe I'll ask him again.