In 1985 we started flying to Europe from SFO frequently. TWA was the choice back then as they had one of the all time best awards: "Anytime," as long as seats were available, 40k for a RT FC UPG on any fare PLUS a free RT FC ticket to Europe. And frequently did 3x miles promos, so each trip to Europe resulted in close to enough for another freebie. Plus, my 2 month old son could earn miles at the full rate even on his FC infant fare, 10% of full fare. He had top elite status at the age of 1.
I knew a "ticket broker" in Newport Beach who (claims he) had beaten TW in a court case regarding barter and trade of miles awards. I didn't need to buy (or sell as the 40k awards were so valuable,) but just a data point re pre-internet and Coupon Connection.