you wnat me to keep this short?
umm, well if he's into driving for fun, the standard MCS is the usual choice. I shouldn't really use the word standard because there's so many individuality option that they're all unique.
If he wants something cheaper, that will still look the part but not go so well, stay in the cooper, and if he's a rev-head the JCW is there as well.
approx new car proces: 32K, 39K, and 47K ish. obviously depends on how you spec them. I know people who have spent skywards of 60.
I personally wouldn't buy used, because you don't seem to save enough compared to the new price. Pluds the new car is better built. has a lot less rattles and niggles. And they've just upped the warranty to 3 years. (about bloody time)
the checkmate and parklane are up-spec things with fancier seats and more gadgets, and stickers. Yes, they are aimed at the 'classier' market - sort of like a perfect pigeon pair for your rangerover, or your x5.
So i guess it all depends on ow much he wants to spend, and what he's hoping to get out of it. there's a MINI for almost everyone, so tell him to get in there and drive one, and he'll work out what spec he needs.
hardest choice is the colour.