Fatboy


Good luck.
I love the Softails, as they have the weight to help keep 'em stable, but still handle the curves and twisties nicely.
To your question on "comfort" and 2-up, I changed the seat on mine from the stock setup to the H-D Sundowner deep bucket seat (my signature picture was before the seat purchase). The passenger pillion is more substantial than stock, so that helps. I have a lousy back, so the lower back support and better padding on the rider portion of the seat is why I bought it ... my wife has her own Softail Deluxe, so we don't worry with 2-up riding...
The seat was stiff at first, but is now starting to get broken in -- believe me, well worth the investment. I agree with some of the other responses that your Sportster may be quicker light-to-light. I spent some time on the Dyna Lowrider and it was quicker than my Fat Boy. All that's OK with me, as I got over the "speed" stuff years ago. Make no mistake though -- you open the throttle on a Fat Boy (or most any other Softail) and you'll know instantly the torque that these engines are capable of. Also comes in nice when you're climbing hills or need to pass an 18-wheeler pretty quickly.
Personally, I like all the FLST softails. My wife zeroed in on the Deluxe early-on. I went back and forth between the Fat Boy and the Heritage, but found a good deal on this bike, so I ended up on the Fat Boy. I'd say ride 'em all and see what fits best - again, you won't be sorry !!!
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