My dad always bought used bikes - single speeds, which we all sort of shared and, I guess, is why I am not a fan of the "single speed" forum. Hey, I learned on single speeds.
My first "real" bike was a Hercules 3 speed Sturmey Archer shifter with both hand brakes and in-hub brakes. This was probably in about 1948-9, when I was about 10.
I went on to a Schwinn paper boys bike which I pedaled up and down steep hills with a full load of to-be-delivered papers loaded in saddle bags on the back rack. That thing was HEAVY! A tire pressure of about 40 was recommended.