I'd tend to try XP first. It won't have drifted as far away from the 16-bit roots. And always remember DOSBox. In fact, rather than a new machine...unless he needs one anyway...I'd say, give DOSBox a try. Good Old Games, AKA GOG, has used DOSBox to get a lot of old games running...as in, 20-25 years old. If it's C code, then *probably* it's DOS code, and DOSBox should work. And, if it is DOS code, I don't think XP will run it directly. You'd have to go ALL the way back to Win 3.1.
And Techy, that's not the problem. The instruction sets are significantly different. The OS calls are different. The 16 bit libraries have to be downloaded. Getting DOS code to run isn't nearly as hard as actually getting Win16 programs to run. I know I got Castle of the Winds to run...an old, REALLY simple dungeon crawl game. It's Win16. FreeGameEmpire has a Win16 emulation setup to help with that.
Oh...and I just tried setting it up again, on a Win 10 box running BitDefender. BitDefender blocked it...they claim the emulator is potentially dangerous. Yeah...well, unfortunately, that is true.
Honestly: there's no guarantee any of this will work. Try Wine; try DOSBox. DON'T try anything later than Win 7.