@retrofreak89 I have some input as far as DosBox is concerned, as I have tinkered with this a bit. DosBox distributed with RetroPie has dynamic recompilation enabled by default, and trust me that's what you want (i didn't realize this was possible on a non-x86 CPU at first). With this feature enabled, and if you max out the CPU cycles in the config file you get performance in the area of a 100 MHz x86 CPU, somewhere between a 486 and a Pentium. I've run old DOS games like Blood and Shadow Warrior on the Pi3 and they work well as long as you keep the default low resolution (320 x 200) I believe. Start raising the resolution, and the games quickly start becoming unplayable. I was also able to install Windows 3.1 under DosBox and run the old strategy game Outpost, which was a favorite of mine as a kid. Outpost ran well under Windows 3.1 (after some arm wrestling with the installer) with no sound stutter or other serious issues. Anything more advanced though would likely have issues however, such as War Craft 2 (which I have not tested, but would be delighted to find out it works well).