Wayne, you don't even have to go back to the 60's for the pen and paper age so to speak. I remember negotiating some charters with Earl and Joe Vigil on the C&TS in the early 90's, and besides a few phone calls it was done with the typewriter and snail mail mostly for contacts and other info. We did have fax machines, which are less and less relevant today.
Wait till we hit the 40's stuff and 50's! I will say things were simpler back then. No worries about insurance as the RR was insured. More like here's the price, thus here is the ticket price and all the rest done through the trip sponsors. They did these things year after year in the 50's and 60's, so I guess it got to be routine to some degree.
Greg