I have a line on a 2005 Mini Convertible S with the JCW package and 36k miles, for $2k more, it would be a 2007 Mini Convertible S loaded up, but no JCW, 21k miles, and for another $2.5k ($4.5k over the first), a 2011 hard top S with 17k miles, loaded with sunroof. Based on what I think I know, I'm leaning towards the first with JCW.

 

Are you factoring in the cost of a warranty? Future repairs?

I'd go for the 2011, but in the final analysis it's your money.

 

Make sure to take it to an independent MINI mechanic before buying any of them, and also have the key fob run if possible to find problems. People who buy cars with JCW upgrades, etc, might push them pretty hard, since speed is their thing. See what has been replaced, too, and what the oil change intervals were...

 

I am not factoring in future repair costs, though I'd like a read on reliability. This is more about the driving experience. I've driven a 2012 so far.
The JCW car is owned by an older gentleman since new, says he has all maintenance records, and he is ahead of the maintenance schedule.
The 2007 owner is the same, has records, great pictures.
The 2011 car is at a dealer.

My other option is a brand new Mazdaspeed3, for just 3 grand over the 2011,

 

I have never driven the 2nd generation car, but others indicate that they do feel different. I would at least drive the 2005 and/or the 2007 to see if you like how it drives. The 2007 is a supercharged model as the turbo was not added to the convertible until 2009. Essentially the 2007 is a R52, as well as the 2005 and the 2011 is an R56. That may not matter to you or it may. After that I am torn. I have the JCW and love it, but two years and 15K miles is a good idea also. What about color and options? Do they enter into your thinking at all?

 

Colors are OK, Purple, Gray, and Red. The 2007 and 2011 are loaded up, 2011 has the most gadgets, 2007 has every option package but the JCW, 2005 didn't look there was much to add in the pricing sites, but the JCW package adds much $ to the value.

 

Definitely drive both generations, they feel different. Personally I'd jump on the '05, but I prefer the first gen, so I'm biased.

 

Do you really want a convertible? (That would eliminate the 2011.) A convertible has other issues to consider as well. (My 2013 cabrio is brand new & just spent a couple of days in the shop having the sensors for the top serviced. I've had it 3 weeks.) The JCW will be a fun drive; the 2007 has the open air option with bells & whistles; and the 2011 probably comes with a decent warranty. If this is your everyday car, maybe having a warranty matters. Once you make a choice, let us know how it goes. And, enjoy!