I was stuck way behind the power curve for years, so my input on this is a little strange. I started with an 8086 box - a Tandy 1000 SL - then upgraded to a 286 in 1995 or so. I finally traded that for a 486DX4 machine in about 1997. It was already behind the times, but that was what I consider my first "Real Computer" - it could run an OS with a GUI (OS/2 Warp, then eventually Win95), and it could play some modern games, but in 1997, there were precious few games I could buy off the shelf that would run well. Just a few years prior, it would have run many of them, if somewhat haltingly.
I traded that for a K6-233, but because I lacked a good graphics card, that only opened a few doors. I could play Master of Orion 2 much better, for example - it worked, but stuttered and kerchunked on the 486. When I upgraded that to a K6-2/350 with a Rage 128, things got better. I could actually look at modern games! But that was in 2000, so it was a fairly limited slice of "modern". That's basically a Pentium MMX on steroids, and it was feeling distinctly low on chooch factor in 2000 and 2001. In 2002, now finally pulling in a junior NCO's salary, I could afford to trade up to an Athlon-750 with a G400 MAX, which was finally in the running as a "modern" machine for its time.
(The real revelation for me was Homeworld. It was playable on the K6-2, just barely. The Athlon hardly even blinked even at heavy action scenes.)
A thought in retrospect - getting that 486 machine when I did was actually a huge, expensive blooper. It was an end-of-the-line build for a 486, with PCI and 32MB of RAM. I suppose it could have gone up to a 5x86/133 and 64MB, differences that would have mattered very little at the time. I should have plopped down the extra bit of dosh for a Socket 7-based rig, even with an el-cheapo P75 - would have been infinitely more future-resistant. But then, live and learn, belike, and that's half the point, now, innit?
Main Box: Macbook Pro M2 Max
Alas, I'm down to emulation.