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Sportster- top heavy, slow handling, fair (at best) braking, value in this case shouldn't be a consideration.
Wee-Strom- Better than average handling for it's class, better braking in emergency situations and in the twisties, lighter, the ability to travel long distances in a single bound.

These two bike are absolutely apples and oranges. But when you break it down the Wee-Strom's ability to be an "everyday" bike should win the day.
 

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Ugly = Extra Insurance Protection

Trying to see the cup as half-full.:)

Being undecided sucks. I'll probably have to move on my gut instinct though. Tough when comparing two capable bikes.
My average wee-strom guy pays in the middle $300 annual range for insurance in GA. Many pay under $300. Although, the lifters are self-adjusting on the XL the wee-stroms ability to hold the tolerance level for the valves is great. You may spend money for valve checks at major services, but those services will be cheaper than the HD majors everytime.
 

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My wife won't even get near the a sporty. Hell, she barely gets near the Kbike and it's comfortable. The Wee with a aftermarket seat is clearly the winner when riding with two. But if the wifey is not likely to go anywhere on a bike I think I would go with the XR1200 and call it a day. Screw fire roads.
 
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