Blimey jazloc, you've just whisked me back in time!
I used to deliver newspapers. I had a morning and evening round for national dailies, and a Wednesday afternoon round for the local rag. (My parents had the news agency so I also used to pick up other rounds too if kids were on holiday or sick etc)
I didn't have music (except if I sang to myself!) since I'm talking pre-walkman days! I loved the rain. Absolutely adored it. It made delivering newspapers seem heroic! It's where I learnt that getting wet didn't matter so long as you were warm. I also had to collect the money too (once a fortnight) and I'd get way more tips if it was raining!
I think I liked the morning round most. I covered more distance on that one as fewer people had the morning paper delivered. But it was mainly for the time of day. During the winter, it'd be dark (I don't suppose I had lights!) and I'd get to see the sun come up. We lived near the beach and on the foothills of a mountain range, and my round included a shore-front street called 'The Esplanade' - a long, straight street. If the timings were right, I'd get to see the first rays of the sun coming over the ranges and hitting the sea. That's a sight I love to see to this day.