Best option would be Dosbox with Windows 3.1. This works perfectly.

If you just want single player, you could hunt down the dos shareware version and run it in dosbox.

There is no single answer. It depends on the game. Some require next to nothing, some compatibility patches and others leave you little choice other than a VM. It best to ask about specific games and you can get a better answer. I had problems in the past with mouselook when using a VM. I don't …

I've never had issues running the original version on 98. Just shit luck I guess? Masterpiece Edition is meant for 95-98, I'd give that a try instead. I've had good luck running the original version if DOSBox running 3.1

Well the issue with that is the games I'm thinking of (Arthur's Thinking Games) barely even works in Windows XP, so I'm not sure it will work with WINE. I'm just trying to get as much information as I can before I try anything.

I'm thinking about setting up a Linux computer for my brother-in-law who is not very tech savvy (he's essentially about 8 years old mentally), and I want to try to make his games work for him. I've already figured out how to make DOSBox work for shortcuts for Windows 3.x games, and obviously DOS …