I started loading in the late ‘80s on a Rockchucker and a Dillon 450. My first press of my own was a Lee Anniversary in ‘95, then in ‘98 I bought a 1050.
The biggest difference for me for reloading then vs. now is really in the process optimization and automation - I used to do a ton of case prep, MANUAL case prep, using multiple steps and hand cranked lathes and screwdriver shaped tools for neck turning, trimming, deburring, chamfering, flash hole uniforming and bevel-deburring, pocket uniforming, and now, I use automated case feeders and electric motor driven tools for most of what I do, and I DON’T do a lot of that wasted energy work any more. Powder handling then was either drop through dies or dropping onto a pan and weighing on a beam - I didn’t get my first electronic scale until ~2003 or 2004, and didn’t get my first electronic dispenser, a used Pact, around 2007, and a Chargemaster shortly thereafter. I built my first annealing machine, turntable style, after reading an article about annealing and chatting with one of my Service Rifle mentors, in the winter of 1998/99. I bought and sold a TON of reloading gear over the years, and I suppose, continue to do so. I’m still kicking around the idea of another 1050/1100 sooner than later, maybe depending upon how successful I find sizing and expanding on a Lee APP to be.
I suppose I have never been a reloader who wants to reload for the sake of it - I’m objective oriented; I’m a shooter who handloads as a means of shooting more effectively, both in ammo performance and cost-efficiency. So I have scrapped a lot of stuff which works, but works slowly.