I just tried both Tropico 1 and 2 on a 64bit Windows 7 and they both work fine, not even using any compatibility options. It may be helpful to know what exactly the problem is that he's having. Being Windows 95-era games, neither Tropico 1 nor 2 will work with an emulator like Dosbox.
Latest news: He has Windows 8 on his new computer. He has several older games that he is going to try again; a more thorough check out.
So, we'll see.
He says he feels a little foolish because T2 loaded up just fine.
It's Lords of the Realm 2 and Warcraft 2 that still won't load.
So he's happy to begin learning to play Pirate Cove - again.
I play on Vista 64, and have yet to find a single game that won't run on it.. (many games i play are from 98-2002)
I do hear one game i own, that i haven't tried wont work, It is the old Vampire "blood lines"
that said, Some games you need to add compatibility settings. Perhaps win 8 you need to do that..
I think you goto the EXE file, under properties, You can set things up to run under win 2k, or XP compatibility. Older games you can force run into low resolutions, or even 256 colors as well.