I have never ridden the Honda Shadow, but it is a nice looking bike. I owned an older Sportster 1200 for 6 years and loved it. Never gave me a bit of trouble, never needed maintenance except for oil changes. Not the fastest or best handling bike around, but loads of fun and I got 50 mpg or better. The newer ones are much better since they vibrate a lot less with the new engine mount design. I traded mine in on a Buell, but would recommend the Sportster to anyone. I bought the Buell because it has the Sportster engine that I like. I also have a Honda VFR800A and it has been in the shop for about 2 months now waiting for parts needed for an emergency recall. This would never happen to a Harley. I think that both bikes are good, but you will have more fun on the Sportster, but get slightly better performance with the Honda. Both bikes are fast enough to get you killed and lots of tickets before that. Buy the one that appeals to you the most.