Great stories, has me reminiscing. I forget how I stumbled on my route in a Michigan farm town, but it was around 30 customers only afternoons after school and mornings on the weekends. After a bit I asked for another of about the same size and had to hustle a bit to make the cut-off time. My dad never helped during the bad weather, he said "it's not my paper route, it's yours". Felt kinda harsh but taught me to suck it up and take my job, all of it, the good AND the bad.
I delivered on a 20" bmx bike with a shoulder bag, I'd deliver one route and it conveniently ended where the papers were for the second. This was in the late 70's and I think I only made about $15-ish per week per route. I thankfully did not have to collect and probably missed a few tips. Don't recall getting any even thought I was very reliable with maybe one or 2 complaints total.
The Sunday's were brutal and with the shoulder bag, talk about leaning! All were around town deliveries but I had to walk each one to the door and place it between the screen door and the main door, every one. I helped my cousin with his route one time where he walked and threw them, so jealous!
I had it for maybe 6 months or so then found a job with the local department store. Great time though out there riding solo glancing at the front page, I still vividly remember 3 Mile Island on the front page.