I tend to hang around in that area of the 8088-early Pentium and not stray further. I have a lot of standard "convienences" to work around.
HARDWARE
The #1 concern for me here is getting data on and off the hard disk, and, particularly with anything 386 or newer, run multiple O/S on the same machine with the least fuss possible. This means I use mostly just ginormous 3rd hand PATA HDD or SATA SSD & HDD with SATA to PATA converters. The only size ceiling I have is for my DOS/W31 machines - 8GB, though I prefer to limit my 286 and older stuff to 3GB or less because there's just no way an XT or AT class machine will use up all 8GB.
When possible I install a "Mobile Rack" - basically a removable hard drive caddy system, so I can pull the hard disk, and plug it into my modern machines to move data to it or back the drives up. This is also a big reason I like the NEC Versa Laptops for a 486/early Pentium era device because it's pretty much the same system but for a 2.5" drive. This type of setup is also handy for when I do want to use a smaller drive to use an older operating system that does not play well with Dynamic Drive Overlays - like OS/2 or Slackware 96'.
Of course everything has some kind of Networking hardware installed. All desktops get a standard 8/16-bit ISA or PCI network interface card, and the laptops get PCMCIA WiFi cards, in particular, the Cisco Aironet 350 series cards because they work with DOS, Windows 3.1x, AND Windows 9x and higher, and from Win 98 on up they DO support WPA encryption making any device using them capable of running on a modern WPA WiFi Network assuming 802.11 A/B is allowed. For Desktop NICs all I require is that I can find the NDIS drivers and Packet Driver.
Currently I'm working out a battery situation for my laptops so I can carry them around the house and not have to rely on having an AC Adapter at the destination.
SOFTWARE
I have a pretty bog standard requirement for ALL O/S I install and intend to use for more than just experimentation and gaming, and that is
- Network Software (to connect to with my modern machines and the other vintage machines when needed)
- A TLS Compliant Web Browser (to download files with)
- Archive extraction tools, usually this is WinRAR but for non-Windows Clients I use other programs obviously
- The ability to use Virtualized CD-ROMs when possible, because honestly I hate having to flip through folders or pull my big boxes down just to play one game
- And Certain Games Get certain things installed depending on the O/S
DOS - MS-DOS 6.22 and FreeDOS (usually)
- Network software is the mTCP suite, which someone else already mentioned, I use FTPSRV in lieu of a network stack, it's just lighter and faster than Microsoft Network Client 3.0, and I don't have to enable SMB 1.0 to make it work. Plus it's shut off when I don't need it (security)
- For internet I tend to prefer to use twibright's Links browser since it's TLS compliant and allows me to access the modern web. Typically I use this for downloading files off the internet directly since it's way less fiddly that way. However I do use it for entertainment and educational purposes as well. I also use Arachne from time to time. for the older computers (<286) I use DOSLynx to access the web which is very rare on those machine, I tend to prefer using BBSes on those for a more "authentic" experience.
- for archives I use PKZIP 250 for DOS, and UnRAR for DOS. I also have used 7Zip Command Line as well for stuff from certain sites.
- I'm still figuring it out but I know there's a way to mount ISO files using SHSUCDEX allowing for CD-ROM virtualization in ISO Format in DOS. Something I plan to utilize when I bump the Versas up to SSDs and put FreeDOS on them.
- I don't use a lot of utilities for Games in DOS, about the only ones are Doug The Eagle's expansion tools for Ultima VI the False Prophet so I have a savegame manager, and can hack the game if I wish (I usually have 2 installs of each ultima, one that's stock, and one with all the Ultima updates added to it with an "E" at the end of the folder).
Windows 3.11 For Workgroups - I only ever use this version of Windows 3.1x, and it's the oldest version I can practically use
- Networking of course is done over TCPIP32B using DHCP with Microsoft File and Printer Sharing enabled
- Web Browser is the one and only Opera 3.62 which is not TLS Compliant, I got the Opera people to give me the key when I asked if I could buy version 3.62 to get rid of the nag screen, I have been known from time to time to kick in the Packet Driver and use Links from there if I need TLS
- For Archives all I need is the mighty WinRAR 2.80 running atop Win32S. It makes life a whole lot easier
- Unfortunatley no Virtual CD-ROM drives in Win3x unless someone knows of a tool like Virtual CDROM for Win9x that worked in 3.1x
- I don't really have to do much for games on Win3x, most of the Win3x stuff is gtg, I might have to install WinG for some things, and Win32S for others
Windows 9x - I keep it much the same for Windows 95/98/Se/ME
- For networking, same deal, TCP/IP over DHCP, Windows Network Shares - have to enable SMB 1.0 in windows 10 though.
- For Internet, RetroZilla - though sometimes I have better luck with Nathan LIneback's hacked Seamonkey
- Winrar 3.80 for Archives
- CD Virtualization is Virtual CD-ROM for Win9x or an older version of Daemon Tools....what sucks is I like VCDR better but it uses VCD files, while Daemon Tools uses standard ISOs
- Certain games get tweaked. Ultima VII parts 1 & 2 and Ultima VIII uses U7dpmi.exe and U8dpmi.exe respectively. Postal is installed using the demo executable and the resource files from the full version because my copy is some old Softwrap piece of junk that the code no longer works for that I bought way back in 2006. The most labor intensive things are DOS games ad Emulators - Virtual GameBoy and Mame get custom Batch files built and then all the EXEs are linked in a DOS Game Program Group and a Emulation Program Group.
Windows NT/2000/XP - It's very very rare I ever use anything beyond 98SE on my machines. Pretty much any game from 1999 onward I can get running in Windows 10 without any issues using the original install media. That said, sometimes I do like to try making my 486 and early pentium boxes endure a bit of torture far beyond what is normally expected.
- Networking is easy, setup on my workgroup, TCP/IP with DHCP, and file shares, same as all the other Windows stuff
- Browser is almost always Firefox - yes, I have run Firefox 10 on a 486 DX4-100.....it's not fun....actually, I'm quite shocked a 486 can run something that new
- Daemon Tools for Viirtualization
- Modern 32-bit version of WinRAR, not sure what version
- Games get tweaked much the same as 9x. On Pentiums though I occasionally use Exult rather than DPMI for Ultima 7.
Now, it looks like a lot of work, I know, but it's actually rather hands off and easy for me after 15 years of this. All my installer CD's have the drivers and updates rolled into them, I have a 1TB external drive that holds all my backed up software and tweaks and configurations, and backed up installs I can just sys c:\ and rebuild quickly without running an installer.