It took me exactly one season. last year I bought my first harley 2000 dyna superglide sport Mind you a very nice bike but not for guys "our" size. I am the exact hight and weight has him. After I bought it I spent $2000 on just trying to make it more comfortable and just couldn't do it.. Changed the seat, bars, forward controls, pegs, etc..Oh and the wife complained all the time.. This winter I sold it and bought me an 03 Road King Classic and loving every second I am on it. Tell him to go a couple of years older then what he want and get the bagger.. IT WILL BE WORTH IT.

Good luck

Harpoon

 

A super glide would be an awesome second bike, behind a bagger of course.