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The bike is considered a "wholesale piece" to the dealer. He most likely won't put it for sale on his lot. He will sell it to a wholesaler, an independent. He will give you whatever he gets as a bid on it. He won't make any money on the piece, but he won't lose any either.
Sell the bike yourself if you are not happy with what he is offereing.
You can guarantee when the dealer goes to sell it he will mention the "factory" rebuilt motor. So yes I think it does help resale, the dealer just isn't gonna tell you that because he wants to get every single penny out of your pocket
It only matters if you sell it to someone that cares! It is sad but true, all of the cutomizing upgrading and repairing you have done or anyone else for that matter is to suit them. In order to recoupe the most money you must sell it to a buyer that understands and apreciates what you have done.