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I may consider the kingpin over the crossroads for financial reasons. How is the kingpin for two up riding, tire wear and where is the best place to find a passenger back rest. Thanks, ride safe and enjoy every mile.
 

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I ride two up a lot. I bought a Mustang driver,passenger, and backrests.They are expensive, but comfortable. I averaged 8-9,000
on rear tires.And about 18,000 on front tires. I just switched tire types this last change.Hopefully mileage will go up. As far as comparing comfort to the CC,CR, or Vision? Well, you should ride each one at your dealer, then decide which you can live with. I love my Kingpin, but my wife wants me to get a Vision for her comfort,as it has more room for a passenger. I told her ok, we can get a Vision as soon as we can afford it but, I want to keep the Kingpin too. She says OK so far.
BTW, we have done some long trips on the Kingpin and enjoy every minute.
 

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Howabout a base Cross Roads with your only splurge being hard saddlebags for both extra storage and lockable. They are only $250 more than the soft bags. Edit: Also get the Vic passenger backrest. It's pretty much the only one available unless you get a Corbin seat.

Should put you close to what you want with a much better two-up riding experience.

I've got an XC and a KP. I'm setting the KP up for single riding with a Corbin Smuggler box on the rear fender. Really fun and flickable bike with great custom potential.

The XC is for when I ride long distance or take a lady along. The large storage area is fantastic for couples.

With the XR you can also add a fairing down the road and even a trunk. All quick detach to get the best of both worlds.

If you can afford to pay cash or get a Credit Union to finance a used bike for a decent percentage rate; you can save a lot of cash 'cause used bikes usually have a lot done to them that you would be doing to a new bike thereby saving you both time and money.

Just food for thought....
 

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I had an 07 Kingpin tour and my wife rides with me 95% of the time. I am 6'2 200 lbs she is 5'3 125 lbs. We had no problems and were comfortable enough for all day rides 400 miles plus. We were tired at the end of the day though.:)
I am pretty meticulous about tire pressure and was able to get 12,000 miles out of the rear tire. The front tire was cupped pretty bad so it was replaced at the same time.
Not sure about a backrest as the tour came with one built into the rear trunk. I would guess that a suitable backrest can be had for 2 to 3 hundred bucks. Two up riding on the Kingpin in my opinion is fine.
If you want to step up then the any of the cross bikes would be a great choice. I think if you look around you can find leftover 2011s, or possibly a slightly used 2010 that may be discounted enough for you to maybe change your mind about the Kingpin.
That being said you can't go wrong with either bike. GOOD LUCK !!
 
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