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I got a 2013 Sportster Iron for my first Harley. I put 19,500 miles on it in 3 yrs and put a lot of $ into making it my own as they say. I loved that bike but it developed a severe knock in the top end and was going to need a complete upper rebuild, new flywheel, and who knows what else so I traded it in a 2016 Streetbob a month ago. I would have kept the Iron a few more years at least and maybe put a 1250 kit on it but really I needed the 6th gear and better two up capability, something I never thought much about when I got the Iron.
The problem is I do a ton of highway riding, and two up, and for that, the SB is better hands down.
If I had gotten then SB first, no doubt I would be really really happy and probably would've saved a lot of $ because of what I put into that Sportster, but I don't regret doing it how I did it at all.
I don't think you can go wrong with any of the Dynas, I would test ride them if I were you and do your research, and pick the one that feels right. If you go Sportster, make sure you're okay with the suspension and smaller size. Those are the main limitations with them.
I personally enjoy my WG.
It handles much like my old Panhead with power to weight, and handling.
The rake at freeway speed is very stable and I've gone on long rides with sometimes 7 hr legs, with little or no discomfort.
There is also a low rider Dyna that looks very cool. http://soundharley.com/Showroom/2016...RIDER-S-323295
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