I ride an '03 883 Sportster. My father and uncles all ride Harleys, so the hog bite was passed on to me. I find most people tend to go up the rungs of bikes as they get older and both finances and needs change. I'll probably ride this little 883 for about another 2 or 3 years. Then it'll be time to trade up. I was thinking about about going to a dyna, but i don't quite think it fits my age and frame just yet. The more i look at it, the more the V-Rod is speaking to me. Speed and style. Not a good bike for beginners, but not an "old man bike".
If i had to ride the fence between a cruiser and a touring model I would pick the Road King. My dad has an '01 with the Harley custom charcoal gray w/ pattern welded steel painted flames. #60 out of 150 or something. That is a sharp lookin' bike. He wants to trade it in for an Ultra now that he has a few more kids in the picture to save a little money on payments. Another nice bike, but kind of the last stage for a rider, ya know.
As much of a Harley fan as I am I have mucho respect for the Hondas. My co-worker who is 20 just bought himself a little '03 Shadow. Great bike. Rides the living heck out of it with no problems. My 883 with less miles has already been into the shop twice and already needs to be re-jetted. His just keeps pluggin along.
Next bike for me is going to be a V-Rod, a Deuce, or maybe a low rider.
Jake