I prefer later years in a series simply because they've had a chance to work out any issues. Remember windows 3.0? total flop. 3.1 was a much bigger success because they worked things out.
I did my research on the forum and various issues in 08 was resolved in 09. Of course many were taken care of by the dealerships in 08 but by 2011 you'd figure they got most of the "bugs" out. I bought my 2011 a little too early and missed out on the iphone integration.