The first computer that I actually -owned- was a Timex/Sinclair 1000 which I bought for around $40.00, well after their popularity had peaked. I had a 16 Kbyte RAM expansion module (which somehow managed to degrade the video output), a microcassette recorder and a 5" TV hooked up to it.
I later moved on to a (used) Atari 400 with a cassette drive. I paid more for the BASIC cartridge than I did for the computer.
Then came a C64. I got by for a year with a borrowed cassette drive before I could afford the big $ for a diskette drive - then the entire year's worth of accumulated data and programs fit handily on -one- of those whopping high capacity diskettes (172 Kbytes!). I eventually had a stack of 4 diskette drives next to that machine - I was trying to learn various programming languages and didn't want to be constantly shuffling floppies for the compiler, headers, libraries and source code.
A used Ampro LittleBoard 1b (a Z80 SBC) introduced me to the joys of having a "real operating system" (CP/M) and got me hooked on assembly language as well.
A used Amiga "1000" was my first system with a hard disk. That made a big difference.
I dabbled with a pair of ancient Burroughs B-20s for a couple of weeks but then scrapped them.
Then I bought my first dos box - a 386SX-20 w/4 MB of RAM and 40 MB HD (I deleted Windows 3.1 immediately and ran just M$ DOS 5.00)... and I haven't had a really cool computer since then.
I've been through a lot of computers since then, mostly freebies, hand-me-downs and scrap of the "Wintel" variety. I keep a few around, hoping the kids will get interested in something that doesn't play "Star Wars", but the wife now says I have to get rid of one (or more!) for every one I bring in the door. Something about "clutter"...
My current computer is a Dell PowerEdge SC440 (with plenty of ram) that I want to get set up with a good linux desktop as the host OS and run some other stuff (SCO, M$) in VMs. I have several older machines running M$ XP, DSL 3.x and maybe still a Win 98 installation.
Tiny Core, like DSL is on my short list of Linux distros not so much for being light weight or portable but because I think I can wrap my brain around it without hurting myself too badly.
At work over the years its been DOS, Windows, Netware, SCO, Solaris, HPUX on whatever platform (including some virtual machines). It seems the hardware's almost irrelevant these days.