Win32 API

Need to maintain app made in the 90's by some retarded intern, it needs to maintain retro compatibility with Win2k and run on Win7+ too, is this even possible, do I need to pay a smelly Indian to do it or just tell my boss to go fuck himself?

Depends what you mean by "maintain", but Windows 8 will certainly run most Windows 3.x apps just fine:

https://www.youtube.com/watch?v=JOj-bAZBhnE&t=36