I've also got this problem 😀
My first PC was Am486 DX4-100, that was intermediate 486-Pentium solution. Despite being nostalgic I wanted to play with Intel in my retro builds (my main home computer always was the AMD since 1997 till today).
So I planned to play enough with VLB that I've never assembled and even seen before and spend more time on Win 3.11. I have everything now and will spend my weekend putting it all together.
For the latest DOS games and early 3D that I missed (college, work and slow 486 didn't allow that) I will assemble either PII or early Slot 1 PIII with Voodoo 2 in SLI. That will be WIn98 SE machine.
There is something that I need to put in-between for games like Fallout, Warcraft 2 and Starcraft, Heroes, Doom, Duke3D, NFS, Diablo and everything I am (was) used to. That was working pretty well on my DX4/100 but definitely will be lagging on DX2/66.
My initial choice was average Pentium. I already have Socket 5 MB and Pentium 100 with 64 (or even 80) MBs of SIMM memory, ATI Rage 3D, ZIP drive and probably will buy 18GB SCSI. But friend of mine is going to send me his old Pentium 166MMX on Socket 7 MB. So now I'm confused. P100 is just an improved version of the stuff I once had, good candidate for classic Win95 with Plus! and everything to make me cry of nostalgia. P166 is definitely something better but it's from some other world, closer to Win98 era, Voodoo or even Voodoo 2 that I want to put in PII. Even three PCs is a lot of space and efforts but four (and so close ones) is way too much. I would better go down to 386, terra incognita to me.
So would would you prefer in the sequence?
386 DX-33, 486 DX2-66, P-100(or even 133), PII-400
or
386 DX-33, 486 DX2-66, P-166MMX, PII-400 (or even PIII-500, 550, 600)
486: ECS UM486 VLB, 256kb cache, i486 DX2/66, 8MB RAM, Trident TGUI9440AGi VLB 1MB, Pro Audio Spectrum 16, FDD 3.5, ZIP 100 ATA
PII: Asus P2B, Pentium II 400MHz, 512MB RAM, Trident 9750 AGP 4MB, Voodoo2 SLI, MonsterSound MX300