Bones, I was a wing man for about 15 years, the older harley just didn't do it for me then. I have since gone to an 08 Softail Heritage Classic w/bags and windshield. I love it. The ride is very comfortable for me with stock seat. Wife likes the ride but the pillon (passenger) seat on almost all the harley models are very stiff and unforgiving. They are fairly inexpensive to replace or have rebuilt. We just finished a three day trip using only the two side bags and no other storage and we did just fine. If you want a classic look with all the comfort, Heritage is the way to go. If you want all the comfort with all the luxuries, then go ultra.