Do you want a project bike you have to work on every weekend? Or do you want to put gas in and ride?
Generally, well maintained is always preferred, even if high mileage, compared to low miles and neglected. Neglected or poorly maintained bikes always suck, and tend to be more expensive in the long run, regardless of the brand. I dont know why anyone would want a high mileage bike that needs work unless they want a project bike to pump money into. Shut up Cooter. In fact, shut up all of you!
For a Ss the 2008-up models are the better ones. They dont make any more power, but have some updates for longevity and driveability. The 2009 models had less than 1000 built, and 2010 was only 283, so those will be really rare.