I have had a great time on my 2001 Sportster Custom and making lots of changes to customize it (keeps me busy in the winter) but over the last 3 years with it I feel that I've over grown it and need to move on.
To go from riding a Sportster to riding a Softail? Is thier a big difference in handling the turns, leans with the weight change between the bikes? Is it smoother to clutch and is it an overall better ride?

 

I started on a Sportster thirty-six years ago and when I went to a big twin I was very happy with it. It's a little heavier and lower to the ground, so take it easy until you learn the differences. It's a lot more comfortable on longer rides too.