Quoting Brian E. Lavender (brian@brie.com):
The Debian 386 installer doesn't work? Install to a hard drive? I have my old 486 in the closet with Debian installed. I can pull it out and fire it up!
Funny story: Around 2005, I was visiting my (now-late) father-in-law in Mammoth Lakes, California -- and mentioned how much in the 1980s I admired _specifically_ the Macintosh IIci, for how hackable and easy to work inside that Motorola 68030-based desktop computer was. And he said "You know, I have one in my basement, and I'd be glad to give it to you."
So, I ended up driving that wonderful late-1980s computer back to Menlo Park, where I installed Debian m68k onto it.
For months afterwards, friends would ask me "So, how does it run Debian?" My answer: "Well, it walks it briskly."
I donated the hardware to the Computer History Museum in Mountain View -- the local and best-case analogue of your aged pet going "upstate".