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Quite the delima but personally I don't see the Vrod being a comfortable two up bike for any length of time. Chances are the Sportster could be made to be more comfy than the Vrod.
The Wide Glide will need a new seat at least for the passenger for it to be comfortable. Maybe shocks too.
The VRod's not the answer. Go with your own thought and get the WideGlide. I have one and love it. I put a mustang pillion seat on it and the wife finds it very comfortable. No comparison if you ask me. My 2nd choice would be the Street Bob but the WG still wins.
Find a Harley dealer that rents them and take one for a day, that will tell you all you need to know. I know here they will let you trade off all day with different bikes if they're not reserved.
I have to agree with those who recommend a Heritage or Deluxe. They are a lot more comfortable for 2 up than a VROD will ever be. If you're used to the Nightster you will slide right into a Deluxe. Just my .02
I don't know that going from a Nightster to a VRod is really a smart move if the intention is 2 up riding. Sure, the VRod will haul ***, but don't think it is meant as a 2 up touring machine.
Agreed, if your concern is your lady, she will not be happy. Plus you can get a Heritage or Road King for a little more money new. Go have her sit on each. Test driving is the key. I've loved the look of many and didn't care for the ride.
If you are set on the Vrod, don't overlook used. Vrods are the fastest depreciating Harley out there. You can get a really nice low mileage one for well under $10k.
2007 VRod - 6,200 miles Buy it now for $10k, but you most likely can get it closer to the starting bid of $8,000.
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