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First, have you test ridden both? If not that is your first step. We all have different impressions of our bikes.
For me, I would avoid the wire spoke wheels and the "beach bars" of the boardwalk but those may be the very things that you find attractive.
 

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I have not test ridden yet due to weather here. The Boardwalk is very similar to Kingpin (I assume). I do like the "big" tire on the Jackpot but need to test ride it also.
 

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The spoked wheels are not a big factor for me.
Next time you get a flat on one far away from civilization, at dusk, near a den of hungry bears, please evaluate your experience for us.

Essentially, the Judge and Boardwalk are the same bike. About the only real differences are the handlebars, wheels, floorboards/pegs, and color schemes.

The Jackpot is a whole different kettle of fish. If turning a bike quickly and confidently isn't high on your list of wishes it might be fine. But you should really demo one right before demoing a Judge or BW. The difference in handling is substantial.
 

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too big tire

although it looks good the oversize rear tire with little sidewall rides hard, being a dunlop makes it worse although it wears well. a penske shock did wonders for my hammer giving a better but still firm ride. a test ride is the answer as stated already because YOU are the ONLY one that must be satisfied. i love the hammer's looks, rode a better lookin 08 but handling was bad due to older style big tire, when i tested my preowned 13 i was quite surprised how much better it was, with the deal i got, trading my 06 sportster there was NO question about buying, i rode it to its new home!!!
 

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I have a Vegas and a V rod with the big back tire. Each bike handles differently. I ride the Vegas on long trips and the V rod on short. On water the big tire is like on ice real scarey. You have to practice the curves because it is a push and not a turn. The rear tire will push you straight thru the the turn. So you let up and lean and give the tire time to turn. Different feel on bumps also, seems more comfortable on rough roads than the Vegas. Just my input but a test ride or do what I did buy both.thumb up
 

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I havent ridden either one, only my Vegas and a Judge, prefered my Vegas,...fat rear wheel looks tough but glad mines got a 180 rear.
Spoke wheels as stated go down real fast if you get a nail, I like the traditional look of spokes but have had a front go on me on my XS650 and it wasn't fun, kept it upright and got it stopped, just as well I was going slow.
Pity they dont make the Vegas anymore except as an 8 ball.
The more I discover, the happier I am with my bike, just got some nice soft rubber grips off ebay to replace the flamed chrome steel wanks that were on it when I bought it...a huge improvement, and the bigger radius where the cables go has quickened my throttle somewhat I think.
Like everyone says, take em for a good ride...In OZ we get a bike for two days , a full tank of gas, and an overnight stay in a Best Western Hotel to get a decent ride...I hear the idea was so successful here that you may get it over there.
Like how can you ride one and not like it? just a matter of finding what suits or comes close and then modifying with all the parts interchangability to come up with tailor made perfection.
Good Luck in your quest.
 
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