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The fact that you are asking us for an opinion leads me to believe that YOU are not "sold" on the deal yet... Personally, I've got my bike where I want it (and it is paid for long ago) and the idea of starting over AND PAYMENTS is not even appealing to me.
Granted, your two bikes will resolve the issue on a bike note. But then the added expense of starting over again is making the purchase that much more of a drain on your personal economy.
If you were so inspired to move forward with the deal, I think you'd do it regardless of what we thought. We aren't paying for it, so it is easy to give advice.
Given that you two bikes are 07 and older, I would consider the newer bike due to the newer frame and brakes. If those issues aren't worth considering for you, I would stay with what you have.
I just traded an 07 Deluxe for a 2011 Road Glide Custom. Did I get a great deal? No, Did I get ripped off? , No....a fair deal...
I found there was more wiggle room on the trade in vs. talking down the MSRP. Whichever way, as long as money comes off the table in your pocket.
I rented the Sadonna orange Road Glide in Scottsdale and loved it, came home and bought one from Cape Cod Harley. Like I said, fair deal....
The rental was 'blacked out'...very nice contrast against the red/orange.....
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