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I've got it worked out now that I'm staying with the Dyna family but I've never ridden a Street Bob. I have owned a Fat Bob. Forward controls are a must and it seems most SB's come with mid control where FB's come with forward controls. But how about the comfort and handling with the mini apes. I've never ridden a bike with an ape handle bar. I've only had drag bars.
Basically, they are the same bike, but I think the Street Bob is better looking, especially if you get an '08 or older before they changed to that dopey looking bobbed rear fender. The Fatbob is a "parts bin" bike that doesn't really know what it wants to be.
Personally, I would go for the SuperGlide Custom...much better looking than either, but again, basically the same bike.
Fat bob is almost 40 lbs heavier than the street bob. I've seen people on both sides say their handles better than the other. I personally like the looks of the SB over the FB. I believe the FB is going to be a little more comfortable ride. Mine hits bumps or small potholes like a mule kick. Im not talking about the pot holes that would swallow a small hatchback, regular stuff that is occasionally unavoidable.
Best thing to do is take one for a ride like chick said.
Street bob is a blank canvas as far as I'm concerned. I'd pick the street bob. I'm partial. It comes down to your taste though. Should drive both like was said.
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