I remember playing around with that idea on a industrial board with a Cyrix 5x86 years ago. Interesting thing about the 5x86 is that it has some experimental features you can toggle via software, for example branch prediction. It gave a noticeable boost but wasn't always stable, hence experimental and off by default. All this works on the MediaGX too since it's basically a smaller process 5x86 with SoC features attached to it. The 5x86 was technically still a 486 era CPU because it didn't cover Pentium-era instructions, but could still compete with the Pentium, especially in mentioned MediaGX which existed at up to 233 Mhz. If you still want to consider this processor even part of the fourth generation is a matter of perspective, I guess. It is for Socket 3, though so would fit the definition of a hotrod 486 and the fastest you can go on such a system. If you can push FSB and memory timing to the limit like I could with that industrial board, potential L2 cache basically doesn't really even do much anymore. (Possible with these very-late gen ALi chipsets you find of these boards, doubt it'd work well with a truly vintage early 90s 486 board, which usually also don't support 3.3V chips, there were 3.3V socket adapters tho) If you want to stretch the definition of the hotrod 486 even further, I guess the MediaGX SBC is one, too. With 233 Mhz probably fastest you can go with a processor that has a 486-era instruction set, especially considering that it's internal framebuffer GPU is connected via PCI. I admit that is really stretching it though.
You can also easily do EGA(CGA, anything digital really)->VGA conversion with some passive components. Of course it'll be 15 kHz, which I don't think anything that even has a VGA connector (which honestly, is not much) will still accept nowadays. There's a nice project to use the Pi to convert EGA to HDMI, which is a lot more straightforward signal-wise than using something like the OSSC, and lossless, which an analog signal by it's very nature can never truly be without some kind of parity. That said, I've used the OSSC with old VGA ISA graphics cards, and the picture is pretty much pixel-perfect. Ideally just need a 16:10 monitor that doesn't throw up at 70 Hz. The small, "portable monitors" are perfect for this and pixel graphics also look better on them than on the huge monitors that are the standard to day. We live in good times for this stuff.
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I thought about my selection further - Going with the 286 would mean no 32-bit protected mode stuff, as the 286 doesn't support this, so all stuff that needs DOS4GW is out. (to be fair though, games of that era are probably too heavy for a 286 anyways) The 386 was a change in quite a few ways so there's quite a bunch of stuff I wouldn't be surprised you'd find in things that don't use DOS4GW but would make a 286 crash anyways. A 386DX would be the safer bet here as everything DOS-era will run on an 386DX, just maybe not at a good speed. That kinda makes the 386 more "boring" as it's basically no different from the MediaGX in any way, just slower. The very early games also usually exist for the Amiga and are usually much better there. If you really spend some time with it you realize how kinda shitty the early PC as a game platform was compared to other offerings. It really only got it's place with 486 processing power and SVGA.
I also googled some parts online and am absolutely shocked at the eBay prices for old PC stuff. Also really surprised that people do things like making new sound cards. Even the benchmark bar mania seems to have gripped the retro PC, guess the consoomers waddled away from the C64/Amiga and found that market finally. It might make me actually part with some of the stuff before the bubble bursts. It's not like I'm ever gonna need it anyways.
EDIT: On the other hand, I'm quite surprised how the prices dropped of on the Amiga side of things. You can get some pretty cool, new hardware for pretty reasonable prices. Very different from the situation about ten years ago.