I'm sure there are going to be some stories of moving up the technology ladder, but I suspect most of them will start higher in the food chain than I did.
I first recorded on an early battery powered mono cassette recorder player back in the 60s. I didn't play, but I can remember recording an acoustic duo by moving the handheld mic as one soloed, or the other sang etc, sort of the reverse of the one mic bluegrass band tactic.
I'd edit by playing back on the cassette player into it's internal speaker and recording on another cassette player.
When I started playing in the 70s I recorded onto an 8-track. No, not a multitrack recorder, an 8-track, those chunky cassettes that folks once had in their cars. You had to make sure that you didn't go past 20 minutes or your track would cut over to the next segment (anyone who had an 8-Track player will remember that "feature"). Still mostly recording solo acoustic and vocals, now in stereo.
Later in the decade I bought a pair of cheap battery powered Radio Shack mixers and ran into the output of each into one channel of a stereo cassette recorder. Mics were now Radio Shack 1/4 plug mics. This made it easier to record with more than one sound source, including percussion tracks I'd make myself and play into the mixer on a second cassette player. As the 80s began I added electronic drums, via the Mattel Synsonics drum toy which I would play "live" or use to make the percussion tracks. And as we all remember the 80s had synthesizer bands with banks of synth to go with their somewhat more sophisticated electronic drums. I had a Casio VL-1. Full control of ADSR on it's single monophonic oscillator--and you could balance your checkbook with it too! I bet Depeche Mode couldn't do that!
Casio VL1
Still mixing down to cassette, but the two tracks while not over-dubable did allow some post recording choices.
Eventually in the 90s I got a Portastudio. 4 Tracks and overdubbing! I never really went full Sgt Pepper with overdubbing on it, in fact I was still recording mostly "live" but 4 discrete tracks did allow better mixes when I mixed down to cassette. I probably started using "real" microphones then, like a Sure SM58 and SM57s.
I bought a Digidesign Digi001 Protools setup right as they came out at the turn of the century and used it to record live rock band stuff as well as solo acoustic for over a decade. I would occasionally overdub, but I never really learned to edit in Protools, despite the product being the popularizer of the whole DAW concept for a great many people. I used a pair of Yamaha mixers by this point and I got a few more SM57, a pair of Octavia small diaphragm condenser mics, and one of those early MXL mics. I actually did all my post-recording editing and mixing in Cool Edit Pro which became Adobe Audition.
In the 2010's I bought my first Focusrite interfaces and while I still recorded live rock band stuff in Protools using them, I started using Logic Pro 9 and then Logic ProX.
I still record "live" playing and I still record things with just a single acoustic guitar, but Logic has lead to my use of Virtual Instruments. Whole string sections, wind instruments, Mellotron tapes without the mechanicals, syths. I no longer own an electric piano, I use VIs. I'll play various ethnic instruments via a guitar MIDI controller. Lots of one-man-band overdubbing, in-the-box digital effects, and more DAW style digital editing than ever (though I still do much less of it than most DAW and VI based musicians do, preferring to play or overdub live parts). My mic selection has improved. I tend to use mid to low priced dynamic mics for most vocals (Shure SM7b and ElectroVoice RE-20), that Octavia pair for acoustic guitar. SM57s still work well on electric guitar cabs, just like they did decades ago.
So what's improved? I never had a high-quality analog setup, so digital recording is what I associate with much better sound quality. Digital editing and mixing is such a boon, just fader automation alone has eased my workflow tremendously. Digital effects are so much cheaper than their hardware equivalents. VIs and soft-synths are amazing.