I traded in my 2004 Ultra Classic on this 2009 Ultra. The 2004 was a good bike, no problems but heat (not like the newer motors are) was an issue at times more so for the passenger, and small frame for two up touring.The 2009 is not even close, it is a complete improvement over anything up to 2008 from Harley. Do not get taken by the appearances of the 2008 and older Harleys. This feels like a totally different bike and it is.
It is more powerful, better handling, better brakes, vast improvement on the heat issue (largely due to new exhaust routing and heat shields keep back cylinder cooler), much more two up riding space, more capacity and you can feel the stronger frame in the corners.
Two slight negatives - harder to find neutral so far, and the side stand lets the bike lean over more than the previous models. So be careful where you stop and put the side stand down. I wish the dealers luck with the previous 2008 and older bikes.