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I think it's a trade off, I prefer a big twin for long trips on the highway. But the rest of the time, I think a Sportster is way more fun to ride. They are like hot rods, you should enjoy it, not just commute.
Congrats! how could you loose? the nightster is no longer produced so they are gonna get harder to find so the chance of a resale if you decide to go a different route is a given. You have to follow your heart and get the bike that calls out to you. it might not be the right one for you , but if you had gotten the Dyna you would never know. plus why buy more than you need? if your happy on a sportster just think of the money you saved and can put towards modding it out.
I myself have a Sporty, Dyna TC, Dyna FXR and a Bagger.
After riding them all stupid hard and treating them like my B1TCH, the Sporty is the only one still kicking on it's original motor. The rest needed rebuilds after a given amount of time and lots of love to keep them from crying.
You made the right choice in my humble opinion!
Now go ride and have fun!
If you want to be racing between stop lights get the sporty, if you want to do more cruising I'd get the dyna, and here is why:
I bought a 1200 Nightster 3 years ago and a 103 wide glide this year. So I have both. They both have very similar performance upgrades; simple and cheap stage ones. That makes the Sporty more fun to ride.
The Nightster is night and day faster and quicker. If I were to race the two it wouldn't be very close. Accelleration is where the biggest difference is.
The Dyna though is much smoother on the road. I call my Wide Glide the Cadillac because the suspension is so smooth. Bumps that would kill my spine on the Sporty are not noticeable on the WG. With the Sporty, I feel every little uneven spot in the pavement, but I actually kinda like that about it!
I bought the WG for long distance trips and 2 up, and it will be much more comfortable. The seat itself is probably twice as wide as the seat on the Nightster. Plus the suspension and 6th gear will be a plus. But I have also done 700+ mile trips on my Nightster and feel I would have been fine if I had a nicer seat (I use the stock one) and maybe - maybe - some nicer rear shocks.
Both are nice bikes, the Sporty will be much smaller and lighter and nimbler but less comfortable, the Dyna will be bigger and slower and more comfortable.
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