Go with the Ultra, preferably '09 or a 2010. The difference between the '08 and back machines is like day and night. In '09 they completely redesigned the machine, and even though it looks the same as the pre '09's,thats all they have in common. I bought a new Ultra last Nov and I cant say enough about the machine. I've been on Harleys for 46 years, and have 3 others besides the Ultra....If your into serious riding, its theway to go. If its just "T T" riding your gonna do (tavern to tavern),then it might be more than ya wanna throw around all the time. Thats why I have 3 other ones.....