As a current owner of both, there's no comparing them. I love my Austin Cooper S and enjoy it as often as I can. Given the original question and for reasons beyond listing, I'm afraid no sale here. The modern day Cooper S would get the nod.
I would let me 07 R56 S go for the right Classic, but then I would go right out and by another new MINI. Oh well! I think the Countryman is a keeper for a few more years, if it remains reliable. Don There is a early titled but late year, Classic available in Denver, $18K-ish, dark blue. If anyone is interested I will post the FB link.
If I win the lottery, I will be contacting MINI to see if I can place an order for a MINI Limo as my second car.:biggrin5: with a disco ball that changes colors of course.