I too have not ridden an 09 or newer, and I've heard that they handle better and I believe it, but my 05 FLHT handles great. They're all great bikes. I have too much emotional attachment to mine at this point, so I couldn't get rid of it. My 88 in. motor will be rebuilt to a 95 this winter, and maybe possibly a 6 speed, not sure on that yet though.

 

I rode an 09 and could not tell enough difference over my 08 to justify any change for me, although I don't get crazy in the twisties.
The build I did on my 08 was worth every penny. I went with the 103 kit with cams and some head work and it was a day and night difference. It really woke the bike up big time.