Got to remember, the prices you see in many of these old catalogues is the list price. The actual net selling price was often quite a bit less. However, it does appear that us Baby Boomers came up through a time of the lowest price shotgun shells. I shot lots of Doves with those $1.69 Federal Monarks, and I bought many cases, not flats, of the early compression formed AAs for $39.95.
I don't see any mention of star crimps in my 1939 Stoeger catalogue, but in the 1941 the Winchester Ranger and the Western Xpert Super-Skeet and Super-Trap have them. I found the review of the "New Remington Crimp" in the Shotgun Dope section of the September 1939, The American Rifleman, page 19. They said it gave slightly better patterns in regular barrels but could see no difference with a Cutts Compensator.