Per the OP we're supposed to start in the 80s. That means my story starts with me as a freshman in college, with one great guitar and one crappy amp. My high school graduation present from my parents was an Ibanez Artist. I had a solid state Custom amp that I'd had for a couple years, big 2x12 combo with white rolled and pleated shiny vinyl covering with metal flake in it, and one distortion pedal. During my freshman year, I traded the Custom for a silver face Twin Reverb. NOW, I was serious.
That guitar and amp would be my only for 2 years. Then I sold the Twin because it was way too big to haul up to my friends 3rd floor apartment to jam. Bought a small Peavey 1x12 amp because it had "distortion!" (Smooth move, huh?).
Once I got out of college, the gear buying started. Within 2 years, I had bought a Les Paul Custom, a Kramer Baretta (had to have a Van Halen guitar, of course!), and American Standard Strat, an 84 Collectors Series Ovataion acoustic, a G&K 250 ML, and a few other pedals. This all lasted until late 87.
At the end of 1987 I got married. When my wife got pregnant, she had a terrible pregnancy. She had gained 20 lbs so far, and 5 months in went into premature labor and lost 28 lbs. She was down to 90lbs and 5 months pregnant! She had weekly doctor visits, multiple tests every time, was on complete bed rest. Said all that only to say this. By the time my daughter was born, I had sold all of my guitars except the untouchable one (Ibanez) to pay medical bills. I'll tell you how things were in the late 80s for Les Pauls... I had a mint Custom. Sounded fantastic, played great for an LP. Listed it on Craigs List for $450 and 4 months later finally took $400 for it. You couldn't get any money for an LP then. Total buyers market. Then Slash came along and the same guitar sold for $1200 5 years later. Anyway... I was down to one guitar and one amp.
In 1997 for our 10th Anniversary, my wife had saved for two years, and bought me the 97 Custom 22 (the natural flamed maple top one I've put up pics of before). The story is, she told me before the anniversary that she knew I had sold all my guitars because of her troubles during pregnancy, so she wanted to buy me a nice one. I showed her several $1000 or so Ibanez guitars at the store that I'd like to have. She said "is that they best guitar?" I said, "no, those are the best, but they're way too expensive." They have 5 Custom 22's on the wall, all different colors. She said "show me one" and at first I wouldn't even ask the guy to get them down because I knew they were retailing for around $3K. At her urging, I got one down and immediately was in love. She later said "I could tell as soon as you started playing it that you loved it." Needless to say, I expected the guitar case when I saw the present on my anniversary. But I was blown away when I opened the case and saw the PRS!
So, that post starts in the 80s and goes to my first PRS in 1997.