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Changes between generations are explained in detail in the FAQ here (http://www.mini2.com/forum/faq.php?faq=new_faq_item#faq_mini_generations). I also posted in another thread explaining quick visual differences with pictures which should prove handy - you can find that here (http://www.mini2.com/forum/3806648-post2.html). :)

Book price for the car you've been looking at (http://www.autotrader.co.uk/used-cars/mini/cooper-s/used-mini-cooper-s-1-6-jcw-3dr-windsor-fpa-201221473599218) is £8k from a franchised dealer, £7.5k privately... although the book price always tends to be a bit on the low side, especially considering the spec of you car you were looking at. I'd say the price was about right, although the mileage may be a touch high, as there are often bits of work needed on the Cooper S when you hit 100k.

The good news though, is that the last few first generation Cooper S JCWs are some of the best MINIs ever made. That's coming from a former owner, and subsequent owner of a second generation model... so, good call. :D

Here are some good first generation buyers guides which should help:

:readme: MotoringFile » MINI R50/R53 Buyers Guide (http://www.motoringfile.com/mini-r50r53-buyers-guide/)

:readme: Buying guide : MINI 2001-2007 | AROnline (http://www.aronline.co.uk/blogs/2011/08/19/buying-guide-mini-2001-2007/)

Keep an eye on PistonHeads Classifieds (http://www.pistonheads.com/sales) - there are always a bunch of nice JCWs, often owned by enthusiasts and generally quite reasonably priced, listed on there.

Glad to help. :)

Comparing the two cars, I think the earlier car looks better in this instance... with the more aggressive JCW styling (especially those wheels which I'm a massive, massive fan of), it makes the newer, regular Cooper S look a little bland? That said, I do love the look of the second gen JCW, with the bumpers & skirts, bigger wheels and nice, fat, shiny exhaust (obviously, as I bought one).

Whether you go supercharged or turbocharged... that's up to you. I'd drive them both first. Having swapped from super to turbo, the newer car does have its benefits (namely fuel economy and tax), but it lacks a certain charm which the supercharged S and JCW have in spades. While there's very little turbo lag on second gen cars, the instant power delivery and crazy whine from the first gen supercharger is totally addictive! A JCW will also feel notably faster than a standard S, which is worth remembering especially if you have high expectations.