Well in my opinion I don't care for the 09's. If you have short legs its going to be a problem as they sit higher than the 08's.
As for the nicer ride. I took one for a test ride and I didn't think it was any better than putting Avons on instead of Dunlops.
Yeah, its got a bigger tire, a little more load carrying cap, frame etc. But that doesn't sell me on it.
Actually, if I were to sell my 08, I would go back in time and buy a harley before they got rid of the timken bearing crank setup, rebuild the engine the way I want it, wheels, tires, paint etc and still be cheaper than an 09 and get exactly what I want.
There are a lot of low mileage older Hogs out there waiting to be had, esp during these trying times
I just wish I would have done that before I bought my 06 too.