I was into dirt riding back in the 2 stroke days. I went from a 125 Elsinore to a 250 Elsinore, to a 360 Yamaha Enduro (it had lights, does that count as a street bike?) I did win a bar bet once, on which would win in 1/8 th mile, between a Honda 350 Four, a Harley Sportster, or a 442 Olds. The 350 smoked 'em, like I knew it would. Sometime last year there was a show on Speed channel where they put a Suzuki street bike (Hayabusa, I think) against a Lamborghini and a newer Corvette. They did a drag race, a road race, and just flat out top speed. One of the cars got top speed. By the way, the BMW (either "S" or "HP4") is now the fastest production bike on the road, but that top slot never lasts long.
HDs are really pretty bikes. So are the new Indians. They just don't do it for me. I actually liked the Kawasaki Drifter, which was a flat-out ripoff of classic Indians. One problem I have with the mega cruisers is the gas mileage. HD does pretty well stock, but they start to suck gas if you modify them. 1100-1200 ccs is about the maximum size to get good efficiency. My bike can get nearly 50 mpg if I don't push too hard, usually around 45 mpg. A big cruiser can get less than my car! It's all about what you want to ride.