I went from a One to a Works, then looked at getting a Cooper S, but there was no comparison... so I'm back in another Works.
The
JCW is definitely worth the extra money in my opinion. With my current MINI, realistically it was a choice between an awesome spec Cooper S, or a relatively "basic" Works... but at the end of the day, I'd rather have a "seriously fast car" (as Fuffy also pointed out) than a "reasonably fast car with loads of extra toys"... even the crappy standard stereo can be excused given the noise that the
JCW makes.
Oh, and speaking of insurance, I had my first Works at 21 and the difference between covering the
MCS and the
JCW was only £100/year or so, so it's not always the case that insuring the latter will cost a massive amount more... definitely worth shopping around!