[Cajundaddy]

It depends on budget. Real vintage old school (50s-60s) guitars could easily be $10k in very good condition. A nice piece of history but IMO they play no better than a modern Standard Strat. I would never gig with such a fine piece of history because if it gets dropped (it will) or stolen I would be forever crushed. It's like racing a 1952 Porsche 356 and going off track at 100mph+.

If my kid was getting serious about guitar and I had up to $1k to spend, I would look hard at either a USA Standard from 2000 to the present, or a minty MIJ Strat from the 90s. Both are really high build quality with good hardware, nice PUs, and they just play great. I own a 2000 USA Strat and out of 8 guitars, it is the one that always goes to the gigs. A sure thing.

Don't discount the Mexi Strats either. It is a lotta guitar for $500 and I could take one off the rack, do a minor setup to taste, and gig with it tonight. They are that good, at least the ones I have played.

Make sure he has a quality amp to play through. About 60% of his tone comes from the amp so I recommend spending at least $300 for a decent one. $500 is better still.