To deal that way, yes he does need to have a C&R license. Yes he will have to send you an ink signed copy. The C&R FFL is an FFL from the Government to collect older non modern arms that are at least 50 years old or on the C&R list. With his license he just can't conduct a retail for profit business with it.
If you can date the Colt as being made in 1949. It would fall under the C&R and could be sold to him on his license. It will have to go through UPS or FedEx though as a C&R FFL cannot send or receive pistols through the US Mail like a regular FFL can.
An enlightened zeal for the energy and efficiency of government will be stigmatized as the offspring of a temper fond of despotic power and hostile to the principles of liberty.
Alexander Hamilton, author of Federalist No. 1. 10/27/1787