I had an 07 MC-S and loved it. My friends were suprised when I traded it for a 2011 Countryman S because I really loved and enjoyed the coupe. I didn't realy need the extra room; but, must admit it's come in handy more than once. My wife and I can bring along more clothes and other items on our road trips. I did chip and lower it. My recommendation is go for either the Countryman JCW or the new Paceman, which also comes with the JCW package.
On the subject of collectibles, usually real collectibles are the first year products, like the two I've already mentioned or the very limited edition GP model in the smaller coupe. Mini enthusiasts or newcomers are always looking for a clean well maintained Mini. The manufacturer frequently makes improvements in new models, sometimes removes things which were included in previous packages and makes them stand alone options. If you're in no hurry, go to a Mini Dealer who has the JCW versions of what you think you want and let the seat of your pants decide. Ask about ordering a Mini equipped the way you want it. On line Mini.com you can build it, print it or send it directly to your dealer, then go in and negotiate your best price. They move little on price, if at all, on the JCW models. Try more than one dealer. It really doesn't make much difference where you purchased it when it come to getting it serviced.