What the OS can see depends on the combination of OS, disk controller and the BIOS. You didn't mention what HW you'd be using, but e.g. 386 era systems will usually not see more than 512MB, pentium 1 era systems may max out at 8GB, etc. No hard rules here, each system is different - to learn more you need to do some googling/reading. One way around limits with onboard disk controllers is to use add on disk controller with its own BIOS (must have its own BIOS) instead of onboard controller. E.g in my PPro200 I have Promise SATA 150TX2 Plus PCI card that supports large SATA disks, I usually don't go over 80GB as Win98SE has some limits here. In my 386 system I have Promise EIDE Pro add on controller that allows the system to see 8GB disks, with DOS 6 limit to 2GB partition, this allows me to setup four 2GB partitions. SATA controllers btw don't have 32bit drivers for Win3.x, so if you want Win3.1 and want add on controller, it will likely end up being an IDE or SCSI, not SATA.
If you already have your HW, i would recommend hooking up a HDD, lets say 80GB a then go to BIOS and see what does the BIOS see. If the BIOS sees e.g. only 8GB, you will need to figure out how to fit all your OSes into that 8GB, which is doable. Often even though the BIOS can see only 8GB, once you install a more modern OS, (i think Win2000), the OS itself will ignore BIOS limitation and directly see full disk size, up to the OS limit. I would however never recommend installing an OS on a partition that's beyond the limit of what the BIOS sees, even if the OS allows it. My experience is that it's going to cause a problem at some point if you try to use some disk utilities for partitioning, defrag, etc. so I just stay away from it. I don't remember all the details, just trying to give you some starting points to research/try further.
I usually try to keep my systems as period correct as possible with the exception of disk controllers to easily use large, fast, modern/reliable drives; and connect them to modern PC for backups for example.
If you're using more modern system, e.g. Pentium 3, 4, etc. (maybe even P2). You should be only limited by OS, the onboard controller will easily support 80GB + size HDDs. The BIOS may even support selection of boot drive upon boot without having to go to BIOS to change boot order, if you prefer to install OS on separate drives.
Sinclair ZX Spectrum 48k, 48k+, 128k, +2
Amiga 1200, 68030/40mhz
386DX/33, ET4000, SBPro2, MT32
PPro/200, Millennium II, Voodoo 2, AWE32, SC-55