I am not much for personal stories. but I have a good one directly on point. Going to take awhile.
As the OP stated, to be a caddy was a serious source of cold hard cash! From after school Friday until they closed the course Sunday night. i could make from $6 to $10. I also ran two newspaper routes, morning and evening, maybe $5 a week. I had not started dating, no car, but I smoked cigars and kept an Ariel motorcycle running. Thing ate parts like I smoked cigars.
This period of bliss came to a screeching (on my mothers side) halt when she found out about my motorcycle, the speeding incident (92mph on a divided 4 lane) (no interstates then) cutting class to ride, no license(not old enough) no insurance, and being brought home by the Ohio Highway Patrol!
Needless to say every elder member of my family ganged up on me. The motorcycle was removed from my life forever.
Being the adventurous (and pi$$ed) person I was at that time, I thought I would run away to the Army. As a member of the Special Forces, we were assigned to many places for many things, often on extremly short notice. On one of these trips (I was stationed at an old WWII air station in Hawaii near Sunset Beach). Our group was loaded and ready to leave when we were informed we would have PASSENGERS! They finally arrived loaded down with several crates of gear, and every one of them was carrying giant brand new Wilson golf bags filled with clubs.
They were the enlisted personnel on the Pacific Area Command golf team. They were going to their next tournament, Their regular plane had been deadlined and we had the only other large freight type airplane that would get them there on time. It is a long boring flight. After a time the golfers took some of our camouflage netting and made a catch net. They started pratice shots and were even using the drivers! Seveal of our group had/or still did play golf and asked to join in, to even including me.
I was never interested in playing or learning about golf when i caddied, it was only for the $, but afterward I made it a point to have played in every country possiable. Could not always have my clubs with me, only some courses had rentals, so I would buy what I thought I needed (second hand mostly) then give them to sombody who needed them.
Never got so good that I didn't pratice everytime I got a chance. That is how i started my addiction to golf. I no longer can play the real thing, but wgt has been a lot of fun and is reasonably accurate.
it's gonna have to be my quarter this time, the story took to long to tell. my nickle wouldn't cover it.