There's so many reasons to like a guitar.
For me, they are in this order: 1. Playability 2. Sound/Sustain 3. Looks
I have a relatively small hand (not helped by a shattered knuckle from a cricket injury) and the neck measurements and shape are very important. At the moment, I'm modding a Washburn Parallaxe which looks cool and plays fast because it had a chunky 'D' shaped neck which felt awkward. I reproduced the shape of my fav neck on card cut-outs in three places and used a Japanese Iwasaki file/rasp and sand paper. Had to get down to the wood thru an odd waxy finish for the wood stain to take. I'll finish the Wipe On Poly with some gentle .000 gauge wire-wool rubbing to replicate the matt finish. Just hops the truss rod doesn't pop! It already plays amazingly, though I've got to finish the job by setting it up.
Any guitar with a glossy, poly finish neck (like a Tele) needs careful fine sanding. The difference in playability is remarkable.
Another factor is scale length - a big difference between Fenders and Gibsons. The shorter the scale length, the smaller the frets. This was brought home to me when I try to play chords now that I used to play with ease when I was younger. They are a stretch. I realised it was because I played a Harmony H77 (still got it - its worth around Ł1,500) and the scale length is shorter than any other guitar I've played.
And don't get me started on the frets! I prefer medium jumbos. You need to know the fret size (height and width) that suits you and periodically give them a polish with Autosol Car Metal polish. They then play like silk.
Makes me smile when guys say, 'that guitar plays well'. Folk should sit down and work out why. It's a science on its own. Then, you don't look at another guitar which doesn't conform to what you know you want.
'Course there's always modding!
I suggest you show these comments to your boy - with a warning - they could seriously eff him up!