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the dyna is considered the riders bike. better handling than the softails. my wife has a softail rocker c the riding position is cramped to me,(i'm 5'7") it has foward controls and i cant strecth my legs out on it. on my 09' superglide custom i added foward controls and i can strecth out nicely on it.
like everyone is saying, the dyna not having the counterbalancer also makes it faster than the softail. just ask my wife!
i will say this if you plan to do a lot of 2 up riding the softail is the better choice.

 

I fell in love with the 1984 Softail, but the novelty wore off quickly.

As stated above, though, you gotta go with what speaks to you.

I was gonna buy a Street Bob when I walked in the showroom, but that Sedona Orange Wide Glide just wouldn't stop flirting with me.

 

Apples and oranges, I like both, Dyna corners so well and Softail seems to ride smoother on the highway. I like the look of a Softail without showing the rear shocks, Dyna has a mean look though lol . Test ride both and see what you like!

 

Depends what Softail you are looking at but...After owning a 2000 Softail Deuce (TC88, 5 speed) for 11 years I can say that the bike is awesome. I traded it in for a 2011 Super Glide Custom about a week ago. Although it was a new frame in 2000 the Softail Deuce was to harsh on my aching back. Here are some of my opinions on both bikes:

Softail
I love the look of the Softail. The hidden shocks give it that older rigid look. The Deuce came with lotsa chrome.
Feels every bump and line in the road. I was beat up after the longer rides.
Little to no vibration at idle.
Love the carb and Thunderslide kit.

Super Glide Custom
I love the look of the Superglides. Comes with some chrome. Since HS in the 70s I always wanted one. One kid in HS had a brand new Super Glide and some of us were way jealous.
Much nicer ride than the Softail. Smoother and handles better.
Absorbs bumps, lines, expansion joints much better than the Softail.
A bit more vibration at idle. The rear fender shakes/rattles and rolls at idle with no one on the bike. The bars shake also but not much really.
Love the fuel injection so far but miss some of that potatoe-potatoe.

You can't go wrong with either bike. Just rent one or at least take them out for a test ride. Sit on them and get a feel for what you like.

 

I have switched bikes several times while riding with my cousin. i prefer my superglide over his softail standard in every situation

 

Best suggestion...go test ride all models mentioned. Make your own decision based on what you feel from each one of them.