What a terrific idea!
I just went through the process of buying a new (to me) boat, and can't stress the value of having someone along to assist. In my case - seeing as I am very unfamiliar with the process - my 'guy' (a dockmate from my marina) was able to give very good and objective feedback. I know he prevented me from making a huge mistake because of his insight.
1989 Hunter 30'
Southern Georgian Bay
The sea, once it casts its spell, holds one in its net of wonder forever. - Jacques Yves Cousteau