You mention looking at a 2011 and a 2008 with a JCW
Tuning Kit but then say you're leaning towards a 2009
Is the 2011 a Cooper S? If so it will be a LCI (facelift) model with the N18 engine rated at 184 bhp. The 2008 Cooper S will have the N14 engine which with the JCW
Kit only puts out 8 more horsepower. The extra horsepower of the 2008 is not worth it given all the problems with the N14 engine. A 2011 Cooper S will also have nicer interior coloring.