This takes me way back in time it was tough duty during the winter though. I was a carrier too in the late 50's & early 60's. I had double duty as a carrier while also being an assistant station captain subbing inserts on Wed. & Sat nights. The trifecta came after the Journal bought the Sentinel. I was station captain for the Sentinel, assistant captain for the Journal and still had my carrier route.
2 of my brothers were captain and co-captain at the north journal shack in waukesha. used to help stuff sunday papers. we would sneak beers into the shack and it was a blast all night. sometimes, we'd take some ad bundles and toss them on the flat beds when the train came by. got busted by the circulation mgr when the flyers were blowing off the train when it passed the central shack where he was working. had a couple other scams too.
The station shacks were made of metal and were very hot in summer without A/C, at least in the winter there was a burning stove with plenty of paper around for fuel. I was a carrier in Milwaukee started right after my 12th birthday. Those winters of -20 degrees were brutal especially on Friday collection day taking off gloves to make change. I remember pulling that coaster full of heavy papers many miles through snow storms. I do remember using a sled several times.
Great experience for any youngster growing up... not sure how delivery is handled anymore.