I've got a Mk4 1.8T as my daily driver (I don't want to put the commuting miles on the Scoob, imagine the fuel consumption : ( , but I'm not going to drive 60 miles each day in any old POS!). My experience of looking for Mk4 Golfs suggests that they are very, very expensive (I am an old VW fanboi so I didn't care that much, to my bank manager's annoyance).
I can appreciate that your son wants something nice and cool to have, but from my experience of owing my first car, the best bit was knowing that it was worth nothing and could basically be fixed for chips. I had more fun in that than in my Scoob (yes, it was infinitely slower, but you didn't worry about taking it cross country or bumping up kerbs or throwing through hedges backwards).
If he wants something newish then Vee Dubs aren't the way to go as you'll be competing against every well financed yummy mummy between here and Buckinghamshire. Try a Pug or a Toyota. If he wants something distinctive, a classic Capri (in good nick) makes for a distinctive, cheap to insure motor that will slay his mate's 106s and Clios and get the girls interested :wink: