"Make the check out to the individual and make them handle the paper work on their side"
Are you sure about that??
I have not purchased anything that way but I know I would not make anything payable to the individual. I would make it payable to the bank that holds the lien and have the account number on the check. This ensures the payment goes to them and the title will be released. My assumption here would be if they didnt pay the bank with the check you make to the individual the bank would just reposes the bike from you as they are the first lien holder and leave you with the hassel of having to go after the individual for the money.
Maybe the dealership can make the transaction easyer as they have a working relationship with freedomroad finacial?