My .02 cents:
First, I would not pay much more than $24K..... and that's only if it is in pristine condition... and with some upgrades, like exhaust, brand new tires, new brakes, and such. Make sure you get all the stuff too... garage door opener module, headset, and, oh yeah, the Gold Key & CVO dust cover.
Absolutely require that the dealer include a warranty... trust me on this one!
I had an 08 SEUC... Copper Canyon & Stardust Silver. Absolutely Beautiful bike. Mechanically, the absolute worst HD I have ever owned. I could start a list of the problems I had, but you probably don't have time. I strongly suspect that some of my problems were just happenstance, because, based on this forum, I had problems that others have not had, but then I also had many of the problems that everyone has had with the 08's too. I almost swore off HD because of my experience with my 08.
I guess bottom line advise from me is: If you can buy it cheap enough with a warranty and if you are prepared to spend some of your money to fix the inherent problems of the 08's, go for it. There is nothing that can't be fixed with after market parts and enough $$$$... just get a steal of a deal if you buy it.