The 502s have only been in production since the 2000 model year, and that was the year that the 2 speed auto was introduced. So chances are good that he had the two speed tranny, unless he retrofitted the 502 to the smaller frame, which takes some fabricating work. The second gear is a pretty high gear (numerically low) so it can get decent mileage (hopefully that guy was not in second gear during the race). The very first bikes had a manual clutch, that was later vacuum assisted. They had a one speed automatic tranny (with torque converter) prior to the 2 speed, but it had a 'compromise' gear ratio to allow decent acceleration and mileage.
The bike's performance limits have been mentioned by others, and it mostly stems from it's lack of aerodynamics, traction troubles from gobs of torque, lack of gear selections, and weight. Compared to the top hyperbikes, it doesn't handle nearly as well, doesn't stop as well, and definitely can't turn as good. But remember, the Boss was designed as a cruiser bike, and when was the last time you saw a cruiser bike that could handle as well as a sport bike? When I test drove the smaller Boss, it didn't handle as well as my buddy's Valkyrie did, but it was very predictable, comfortable and surprisingly forgiving. Race-bike performance is nice, but that's not what everyone wants all the time. I love my fast sportbikes, but there's those times when I'd rather be on a cruiser, just tooling down the road at a relaxed pace and enjoying the engine's music.
I'm sure most of you have had experiences with the older muscle cars. Many say they don't turn/brake as well as the Viper, but still like the brute tire-smoking power they had. The Boss is all about brute power (and comfort), and that's what makes it fun. The bike isn't the prettiest machine in the world, but it's basically a naked cruiser bike with an enormous engine and radiator. Too me, I think it looks pretty cool with the engine sitting there all exposed. I can't think of anyone who thinks the naked engine on a rail dragster looks ugly. The fuel tank is huge, but it just has to be.
I guess you just have to ride one to understand why someone would/could like one. It's actually more fun than you might think, especially when you can do a 100 foot burnout effortlessly. I'm gonna have one custom built with a 6-71 blown 700+ cubic inch Donovan aluminum big block, one of these days...
Sorry for the dissertation!