Nashville Tennesean - about 1964 + 1965. A smallish route, 60-70ish papers, if memory serves.
Maybe $25 per month, after supporting the deadbeats who wouldn't pay.
I had a good sized apt complex (maybe 20 papers) on the route which was excellent for speed & bad for collections.

After that job was Sat. work at the A&P grocery for $1.62 per hour.
More monthly income and a ton less effort.

edit: yeah - zombie thread from 10 years ago = How did I miss it the 1st time around?
And I too delivered with a bike, the family balloon tired POS with basket on the front. Wed was ad day and required 1 over-the-shoulder bag. Sunday required 2 shoulder bags and was a bit_h riding the two moderate hills. I could roll 'em real tight when I had to. What kept me at it for almost 2 years was that the pick-up point was only 1/2 block from the Krispy Kreme Donut Shop. What a smell at 5am on a crisp cold morning!