Wow, Sam. you’re experience sounds something like mine. I started with 45 rpm records, then 33 rpm records, then 8 tracks, then cassettes, then CD’s. And now everything is on an iPod, which could choke and croak at any time. Why bother?
Yes, I pretty much ran the gamut myself. As a kid, I collected a few vinyl 45s and LPs. Didn't have much money the so most of my collection was obtained at flea markets and such. Then it went over to cassettes before the CD revolution. My father collected 8-tracks but I never had one myself. My father had a pretty awesome country collection: Johnny Cash, George Jones, Wanda Jackson, etc.
These days, I mostly just stream Sirius/XM radio, Pandora and Spotify playlists. Not sure what will be next.