In general I agree with you, but if we're talking about buying a guitar without knowing anything about guitars (i.e. how to play them), then the guitar has nothing to say to you, even though it might speak to someone else readily. Buy a $50 Squire on CL, and see what happens. When you learn a thing or two about it's operation, then get picky.
I stand by my recommendation and think that an instrument can still be more or less approachable to even a novice. Aesthetics, weight and feel are immediately apparent to anyone. Plus, he's not 10 years old. Chances are he's held guitars before and may even have an idea of what characteristics appeal to him? Or maybe not. Perhaps I'm wrong, I know very experienced guitarists that have purchased guitars via eBay that they LOVE. Of course, these are vintage, bad ass guitars and not $50 Squires. Bb, what was your first ax?
My first guitar was an imitation Gibson with the hummingbird pattern on the pick guard. It was a gift for my 12th birthday from my dad. I played the shit out of that guitar, bringing it on family trips and such like a toddler with its blankie, although jamming Nirvana on a crappy acoustic never did sound quite right. I got my first electric guitar a year or two later; it was a black Squire Stratocaster. I pawned that eventually for a real Strat, which eventually I sold in favor of a P-Bass, a guitar I still have that is the last in a continuous succession of instruments.