Personally I would not consider a 2008 over what I have now. I have it the way I like it, it runs good, and I saved for many years to buy it!
I made sure it had the features I wanted before I bought it and that it met my needs and wants.
I also am the type of person that when I get a new car/truck/or bike I keep it for 9 or 10 years because I research before I buy and I never by the first year production of anything. I want the bugs worked out first.
Short of theft or accident the only things that would sell me on a newer Harley would be if they could make one more dependable and with more power in an easy to maintain format. I know I am probably in a minority here but if Harley could make a water cooled shaft drive touring bike so it runs cooler with plenty of power and handled safely with no wobble I would consider it after maybe 2 years of production. I know it sounds like a Goldwing but I still love the sound and feel and looks of a Harley.
If the EPA and the "green people" don't let up it may mean the end of Harleys as we know it and it will be harder to run or maintain in the future if alternative fuels are the only thing mass produced and things like our oil and other fluids become banned Hazmat items with no easy way for purchase or disposal. (think of leaded fuel or the old freon for homes)