If you're thinking of doing something similar, either in a VM or on compatible hardware, I recommend Windows 98. You get FAT32 which gets you larger hard drives, where pre-OSR2 Windows 95 has FAT, where the max hard drive size is 2GB, you need to divide larger drives into multiple drive letters.
Windows 98 also gives you easier third-party ways to turn on universal USB flash drive functionality. Without it you need a driver for each flash drive, good luck finding that today.
Windows 98 is basically the pinnacle of DOS-based windows for gaming, Windows ME takes away some DOS functionality.
I would recommend Windows NT 4. Because it is NT-based it runs well on modern systems and VMs without special patching, and even has VirtualBox integration. Yet it has that lovely Windows 95 UI (though slightly different in a few places). If you prefer the Internet Explorer-infested 98 UI, you can install the Windows Desktop Update in NT 4.
It can run most Windows 9x software, though games may be a problem. It has Pinball though!
In my experience, 86box tends to require a lot more resources than PCem. For example, a standard PC XT configuration will peg a whole CPU core in 86box at 100% while PCem will use just 10% of a single core. I don't know if it's a bug but it makes using 86box on a laptop uncomfortable.
