Last year bikes were cheaper IMO. There were a ton of left over 07s under msrp and used bikes were much cheaper. This year, it is a different story. Dealers are much tighter on supply. My dealer has 5, 2008 bikes left and they are over msrp on them. I have noticed the great used bike deals are gone. The HD CFO mentioned that used bike prices had increased 4 months in a row, because of the production cut. In other words, I think your deal is fine and I would look for book values to come up some over the next year.
you did very well, i prefer the 88 5 speed myself just do a search on here on heat, 5th gear noise and other complaints for the 96 6 speed, also i believe yours is carburated and from what i have seen on this forum most carb bikes get better mpg when properly tuned. you would think efi would get better mpg, just what i have noticed.
I think it's 2 thousand high. At 24k the cam chain shoes might be close to giving up the ghost, unless he has had them checked recently. Throw 4 g's more and you can get a 2009, with brand new everything.