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@gree: strongly. I would also think strongly about what type of riding you will be doing on a regular basis. This isn't necessarily what type of riding you'd like to do most of the time.strongly suggest renting both the bikes you're considering. You have the Dyna family and considering 1 softail and 1 touring. you'll get more suggestions if you state why your not happy with the bob.
I rented an EG Classic over the weekend. I sometimes regret buying my Fatboy and subsequently dropping lots of $$ into engine upgrades and what not. The bike is just not suited to riding with my son or my wife nearly as well the touring bikes. So as part of celebrating our anniversary we set up with sitters to watch the kids and planned an all day ride on EG. To say the least, it was fantastic, the new 09 Touring bikes are everything I've read.
And then this morning, I hopped back on the Fatboy and went to work. And then I remembered why I got this bike and how much I still love it. This is the primary type of riding I do, all by myself. I have no desire to see the Fatboy out of my garage.
Point being, take your time, go rent bikes you're thinking of buying and maybe those you weren't. You may find you want to just stay with the Street Bob. But if you decide on something else, you'll have made the decision having educated yourself.
Good luck and ride safe!