I delivered Newsday for several years. It was an afternoon paper at the time, so I’d pick up the papers when I got home from school, get on my bike and spend about an hour each day. I don’t remember how much I got, but I did earn something. Collecting was never much of a problem; very few people stiffed me.
I also delivered the New York Times in my school. That was more of a drag. I barely broke even and it meant I had no lunch hour. About all I got out of it was a free copy of the Times each weekday.
I delivered the Pittsburgh Press Sunday paper for a couple of years. i had a route that was about seven miles long, and my father would help me with the last three miles- it was up a mountain road.
The biggest pain in the posterior was assembling the papers. They came in 3 sections, and head to be placed just so for all the people who liked their papers that way. I’d get up at 5 am to start this.
Collection was fairly easy- most customers had a place reserved for their paper, like a box, sheltered from elements, and the 50 cents was usually right there. If they didn’t have a box they left the money between their storm door and main door.
I helped a friend deliver the local daily from time to time- a different paper altogether but most of the same customers.
My parents were tight with money, so this is how I made my spending cash. I made 8 cents a paper, and 5 cents a paper for the daily. The only collection problems were old people who forgot to leave the money out, and I usually let them slide until next week.
The papers were heavy, and the weather made it suck from time to time- can’t bike in the snow. (This was in the days before mountain bikes and BMX.) And I had to get up early- never fun for kids. I think I was 12-14 then.
I delivered the Detroit News & The Detroit Free Press (ages 10-12), on Sunday the News and Free Press were the same paper (what the hell was that about). About the only thing I didn’t like about it was collecting the money. My route was about 8 blocks long, and there was at least one deadbeat on every block. You susposed to suspend service immediately if they don’t pay, but guess who they’d call if they don’t get the paper. My favorite was this little old lady on Linden. She’d never have her money but would every so often give me $2.00 “for my trouble” on Sundays. Because we always had 5 or so extra papers, I cancelled her a gave her my one of my extras.
I never delivered papers but I have a brother and sister who did during the 70s, she took over after he graduated high school. Their route was 10 blocks (the entire town at the time) and customers paid about $3 per month. I have no idea what their share from the Kankakee Journal was.