I tried to trade at Castle back in the Spring. Same trade you're proposing, i.e. an '08 R3T for a '14 R3T ABS.
I really wanted to trade with them. I prefer to deal with nearby folks, and they're my closest dealer.
However, they pretty much wanted me to pay retail for their bike, and they wanted to give me a couple of thousand under book value for my very nice, low mileage trade.
I then tried to trade with Pandora down in Chattanooga, but they were even worse. They wouldn't make me any offer on my trade. They basically didn't want it. A Triumph dealer, explaining to me that the Rocket IIIs are too hard for them to sell.... go figure.
So I sent Randy Baxter (Baxter Cycles in Marne, IA) an e-mail note asking about trading with them. I'd dealt with them before with vintage motorcycles. They're very honest, and seem to have an excellent ability to move motorcycles in both the US and overseas. They're pretty big in the vintage bike export business.
In any event, Jeremy called me back quickly, I sent him some pictures, and we worked out a deal that was $2000 better for me than the one offered to me by Castle. It was pretty much all in the trade value of my '08.
I drove up there with my '08 in the trailer, and drove home with the '14.
They put my '08 up for sale at a fair price, and they sold it in the Spring market. They made money on the deal, and I have been very happy with the '14 ABS.
So ... Baxter is also quite good about working out shipping details. In fact, they've actually brought a trailer to my house to pick up a vintage bike ... Randy makes trips around to get vintage bikes whenever he gets enough leads to make the trip worthwhile.
I would have liked to trade with Castle or Pandora, but even with the expense of the trip up there, I came out $1500 to the good by going to Baxter.