I have a high-end 486 motherboard with four 72-pin SIMM slots and PCI slots that accepts up to 192MB of RAM. For some reason it can't handle four 64MB SIMMs so it won't do 256MB, but it'll handle three fine. Or one 128MB and one 64MB one. But adding anything more makes it not boot and it seems to be a chipset limitation. At one point a couple years ago I had it maxxed out at that complete with an AMD 5x86 120mhz, PCI USB, video, and sound cards and Windows 98 and it did work but... other than for funsies there's no real point. I could have installed modern Linux on it but again, not something I really need to do or would miss not being able to do.
I think it would have probably managed Windows 2000 for fun, but again, not really. It's just a toy at this point and I don't see a use a case for it. I think there are some embedded cores based on the 486 instruction set like the Vortex86, but I believe the current ones have implemented enough (or maybe even the complete) Pentium instructions to run more modern stuff. And nobody probably needs to continue running the latest, current updates either given they're embedded systems.