I started in 1966, loading 45 ACP. Friend's dad had a 1911 AND a genuine "Chicago Typewriter". He'd let us shoot them (with adult supervision), but we had to provide our own ammo, so he taught us how to reload. Sometimes one of our dads would take us to buy components at a couple of LGS's, but other times we rode our bicycles. Imagine 11 and 12 y/o kids doing that today. We usually did our reloading on Friday nights, and my friend and I would load for hours, sometimes all night, on a Rockchucker. The sizer was a standard non-carbide, so it took a lot of time cleaning lube off the brass with old rags. Then on the appointed Saturday, one or both of our dads would take us somewhere (often our farm) where we'd shoot it all up in a couple of hours. Then we'd go home and clean them thoroughly. We burned a lot of HP-38, Unique, and Bullseye through those two weapons.
Our parents didn't give us money to buy components with, we had to earn it ourselves. Both of us had multiple side-jobs, besides normal chores. Bought my own tools in 1969.
As noted earlier I also started on 1966--but was the first handloader in the family. A next-door neighbor (and good friend and co-worker of my father) handloaded, but he basically did it to save money. The only rifle round he loaded was the .30-06, for his "sporterized" 1903-A3 Springfield.
I bought a "war surplus" Mosin-Nagant rifle for $10 and he helped me sporterize it, but I had to order a Lee Loader (the hand tool) and Norma brass from a local store, the Powder Horn in Bozeman, Montana--where I was born and raised. It was also only three blocks from our house, which was handy. Also bought my first bullets, powders and primers from the Powder Horn, but my first two loading manuals.--both of which I still have. The first was the Speer #6, which I bought without checking whether it included the 7.62 "Russian." It did not, which is why I have a Lyman manual from the same year.
Not long afterward bought a Marlin bolt-action 20-gauge, and also used a Lee Loader for it, which worked well.
Paid for all of it with my paper-route money.....
