Here's my 2 cents worth. I just traded my 06 St. Bob for a Softail standard. There was nothing wrong with the Bob, just some little things I found irritating. I hated the ignition in the neck, now it's on the dash. I also think there is a ton more accessories for the Softails. IMO, I feel that the Softail rides a little more bump free compared toa Bob. The Bob does handle a lot better, esp. in the twisties. I got the standard because I didn't want to pay the extra coin for what I would strip off anyways from the custom (wheels and seat, sissy bar). I do have to say the silver engine is a bit drab though. I wanted the fat tire and the better gearing of the 07 models. I do think the Bob is a better bang for the buck, esp. the 07 models. They will both treat you well... Over and out Krusty...

 

I bought a street bob in 06 rode it for about 3 months and loved it. Then I rode a Deluxe and was blown away. Its a bit like most folks are saying here, the dyna handles better so you can get more agressive in the twisties - but it aint alot better - just better. But the deluxe (softail) was way more comfortable for me in the long haul. For freeway and long highway rides the deluxe is waaayyyyyy more comfortable for this rider. Feels way more stable at higher speeds, can ride it longer more comfortably and it just fit my taste in what I wanted and perceived my dream HD to be. For long trips, the deluxe just perform better in varied conditions than the bob imo. Wider front tire handles expansion joints and stuff better. I feel like I'm sitting more in the bike than on it too. I like floor boards, larger gas tank and retro look. And like others have stated, their are more accessories built for the softail. The absloute only thing I liked better about the Bob was the rumble/vibration at idle. But after I added stage I/bassani road rages etc., it sounds great at idle but still doesnt vibrate. The deluxe is more of a cadillac and thebob was more of a chevy. I do love the looks of the wide glide though, I'm just too short for it 5'7". All this said, I haveonly ridden the Bob, Heritage, Deluxe and RK and never ridden a softail custom or standard. Seems to me that the softail needs to be a in a Fatboy-Deluxe -Heritage package to get it's true essence. Otherwise, I probably would get a dyna. But thats just me. Guess thats why they make so many models, everyone has their own ideas of whats hot and whats not.