My first job was also paper boy (unless you count babysitting). I delivered the Today's Post when I was somewhere around 12. It was a local paper, and as far as I know, it doesn't exist any more. Amazingly, Google doesn't even seem to know about it now.

I can't actually find a photo of the type of attachment that I had on my bike that was provided by the newspaper company.

I had a bag from the newspaper that was something like the one in your 2^nd photo, but I just carried it over my shoulder. I never attached it to the bike. I was riding a ten-speed, so I doubt if it would've hooked over the handle bars like that.

There was one house at the bottom of a really big steep hill - probably half a mile, and I hated the fact that I had to ride all the way down and up again for one single house. The couple who lived there was really old, and they tipped well, though. In winter time it felt like they kept their house at about 90 degrees.

there was some danger and surprises such as the rubber bands snapping and whipping my hands

Yeah, that really stung in winter time...