Hey Lance,
I have only used the sport so far, and I have been happy with it.
I have not changed the original blade it came with yet, but I think it may be time to soon; getting a little more pull and resistance now.
I think it's more of a preference thing. I feel like I may have trouble with a classic because I am used to the sport. The wheels definitely help you roll smoother, and since I haven't seen a classic in the store I dont know what the part you rest on your head looks like. I think the shaving arc is still the same, but we may have to check with the HB guys on that.
My current view on it is if it ain't broke, don't fix it. Heck, I'm so worried that when I change my blade I'm going to get chopped up, because it seems to have happened to some of the other guys. But I will have to eventually.
I will let you know how it goes.
Joe