I delivered the Times-Union in Albany, NY for a few years. I'll guess I was 12 - 14 and I had what was then a suburban route. I covered about 3 miles, and a few small hills. I had some sort of 26" bike, typical of the day, but by saving up I was able to buy a new bike. I'm guessing it was about $50, a ton of $ back then, but this bike was special! It had an "automatic transmission!" It was a "Monkey Ward" (Montgomery Ward, a Sears Roebuck like catalog company) bike. It had a coaster brake, but you could also shift gears from low to high by back pedaling slighly. It was really nice having the gear on the few hills, but there was a design flaw. The axle had a thinner area that allowed the shifting to occur. That was a weak point, and the axle failed at that point twice. It was then I returned the bike and went back to a standard bike.
Delivering the papers was not bad except for Sunday when the papers were 2 or 3 times as big, requiring several trips back to home base. Collecting was another PIA, trying to catch people at home and dealing with 'slow payers.' But Christmas was great when people would give you a buck or two Christmas gift!