Not to get on a Harley bashing mode, but I think the days of high trade in and resale are over. The only thing I base this on is the fact out local Harley dealers are advertising like crazy (Noteably Gail's HD) about overstocked 2006's, left over 2005's, and all of the trade ins they need to move. One ad said they had something like 250 NEW HD's in stock, will accept anything at all on trade (as long as it doesn't call you Daddy), low interest rates, poor credit and bad credit OK and so on... Wheelin' and Dealin' like crazy. If they are cutting their own gross to move bikes you aren't going to get a great trade in allowance. And last time I looked at the KC Star want ads there were literally hundreds of used Harleys in there. Me thinks the HD market is over saturated.
It might be a good time to get a Night Train... if thats what ya want..