I run my board on Windows Server 2003 32-bit on a standalone box.
My test system is an Oracle VM VirtualBox on my Windows 10
workstation. With file sharing and RDP, BBS management is a breeze!
I am convinced that if you want the 'old school experience'
then Win32 is the only way to go!
Shrug, I have MS-DOS VMs, in VirtualBox, I load XFS for nfs client, mtcp for time sync is the only thing I'm using, and rlfossil for my telnet server. VirtualBox does make it easy to jump around from one VM to the next. I'm not sure about your Win32 angle :) Aside from DOS everything else here is linux driven.
Spec
--- SuperBBS v1.17-3 (Eval)
* Origin: (21:3/101)