I didnt read all the replies, im just answering the main question so...
The main problem I had with the JCW is the front wheel drive on snaow, the torque, the hard rubber run flats, and light weight of the car, made it somewhat improper for snow driving. But that would be specific to my area, Chicagoland. If you are in Socal or somewhere where the snow is minimal, this would not be your situation.
Another issue may be the run flats tires, they are stiffer than normal tires, they are stiff to run flat, there is no spare tire in the car. So, as you see the small trunk is the third issue, you can fit a few things in there, actually I fit two 20x20 boxes and another 24x12 box with seat down. So there you go, can you live with those sacrices? Many cars have sacrifices that you will have to make. Example is Subaru, great performing car, lean mechanical complications but the design aesthetics makes you look away. The Audi TT, its a 2 seate2 with a 5 cylinder, why would you want 5 cylinders on a 50K car. The final option is the elusive M135, if you can find one that hasnt been marked up, thats right marked up from MSRP, you could have a nice rear drive ride, But again, not much for the snow. Mini does make a 4x4 cooper 4 door JCW, that is interesting, and if they can fit that into a 2 door model, hmmm.

Oh also, as you become more immersed in upgrades, you will find that the hood will be subjected to alot of heat from the turbo. They sell an app for that, called a heat shield. I would say that there are small issue with the car, but the aftermarket parts world has come to the rescue in a big way. I mean you can get a ton of stuff to prevent this or upgrade that. One of the coolest kits I saw was the rear diffuser kit and ram air integrating the hood scoop feature.

Buying a new mini
 

Just bought a 2010 hatchback s with just 16,500 on it. Not certified but I did buy an extended warranty. Wrestled with buying new and a relatively low mileage car. Couldn't resist as this car is really clean and runs terrific. My driving is limited so a low mileage car vs new was a savings and hopefully good outcome down the road.

I purposely avoided an 08 or older model regardless of miles. Things I read indicated some of the early bugs withi the 07 model change were worked out in 09 and beyond. Time will tell.

Good luck with your purchase.

Doug

Looking at possibly getting a Mini Cooper S, but this is way early in my buying process. My timing is next summer, maybe late summer. Trying to keep this below $10k, so I'm focused on '03-'05. Six-speed is a must. Want something small to fit in the third bay of the garage with room for lawn mower, etc. Thought about a Miata, but really need a back seat for 10-yr-old son and his friends. This would be mainly a grocery getter and foul weather car so I can leave my garage queen in the garage.

Sure wish this thread had gotten some wisdom posted up from some of the veterans here. I've heard "stuff" about Minis, and I don't know if it's just a few guys with sour grapes or whether I really need to watch for these things. Didn't know about the squeaks, so that's one more to add to my list.