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I traded my 2007 Street Bob for a 2010 Heritage. Absolutely no regrets. The SB is a great bike, but you'll see the difference if you make the deal. Softails are one smooth ride and styling can't be beat, IMO.
I traded my 09' Street Bob for a 09' Crossbones. The Dyna's are more nimble and for someone who wants a sportier ride, but the Softtails are better for long extended riding and cruising. Outside of this, which is my personal opinion, I like the looks better too.
I owned nothing but softails before I got the Wide Glide. The softails are nice riding bikes, good styling, and fun to ride. With that being said, after riding my Wide Glide it'll be hard for me to go back to a softail. For whatever reason a dyna just seems to have more of a "fun" factor...Can corner harder, seems like it's more powerful (even though it's the same engine), and still somewhat comfortable on long trips.
Certainly it is a subjective decision...you must ride each. In my case I went from an '04 street glide to an '05 Deuce 3 years ago and never looked back. Fatboy rental is what put me on a softail and the Deuce/Fatboy decision was difficult. My opinion is shared by a lot of folks that you sit IN a softail and ON a Dyna. Styling is an area that divides riders too..but again it is subjective so it is YOU that makes the call. Many feel the Dynas are more "nimble" but at very low speeds I prefer the Deuce and yes there is a bit of rear looseness in softail that is more apparent than Dyna line when pushed cornering at high speeds. I swap rides with my neighbor who rides an '09 street glide and it is a nice ride but even he likes the Deuce better for position and seat comfort. Your call. John
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