I started a similar thread back in 2012 along the same lines, "How we got started recording " but I think it's a good idea for a redo because there are many new contributors here now
Like others as a teenager I tried with a simple stereo cassette in the mid 60's but it sounded so bad I gave up.
Thru some fortunate circumstances in 2002, I got the chance (for free) to knock out about 8 songs in a high end Post Production studio in midtown Manhattan one Sunday afternoon. It was a Pro Tools TDM system with acoustically accurate control rooms to record in , and using two Neumann U87 ai mics, one on my acoustic guitar and one for vocal. I was hooked.
When I got back to Wyoming in the spring of 2003 I bought a home studio system. A Digi- 002 8 channel console mixer, with Pro Tools LE , an Apple G4 laptop. And an inexpensive Studio Projects C1 LDC (I think) mic, and dove in.....And some KRK 8 " monitor spks.
As jim1960 noted the pres in the 002 were also marginal at best, and coupled with the cheap Studio Projects mic I was frustrated when A/B ing against the CD of songs I recorded in NYC. As noted it was quite brittle sounding comparatively.
I bought a Focusrite ISA series 220 single Channel Strip which was slightly better sounding .
Then a Apogee Rosetta 200 2 channel converter again some slight improvement.
I finally gave up on the Studio Projects and went in search of something better ended up with a pair of Shure KSM 44 s good improvement
A few years later I decided to try to find something like the Neumann U 87. Sold the 44's and ended up with a Brauner Phantom V . Pretty significant improvement.
I then set out to get a Mic Pre-Amp, after about a year of searching I bought an A Designs MP2A tube 2 channel pre , after playing and singing through one.
Next in January 2011 I made a big change. I sold the 002 and got an Avid Omni interface with HD Native PCIe card and an Apple Mid 2010 Mac Pro Tower.
I also enrolled in a 12 week online Pro Tools production course, at Berklee Collage of music
Then in aprox 2013-14, got a Schoeps CMC 6- MK4 SDC for acoustic guitar
2015 ,sold the KRK's got a pair of Amphion One 18's and an Amphion 100 watt amp.
2016 got an IGS Tubecore 3U tube Mastering Compressor
And finally early this year I sold the Schoeps got a pair of AEA N 22 ribbon mics an ADK Z-Mod 251 LDC tube mic .
I am pretty well set now just need to try to get my performing, recording, and mixing chops, up to somewhere near the level of my gear