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I'm doing this on a daily basis with problem. However, in 2003 I had great problem compiling a Win3 program written in 1996 (only 7 at the time, not yet 20 year old today) program to run on Win2000.

The secret to being able to do this properly is to keep a curated development environment that has the old tools/libs in their proper form -- which I suspect is why you don't have a problem (20 years ago you had VC5/VB5 - do you compile the same program with VS2013?).

YMMV, but my experience is that the Microsoft environment is worse than Linux in this regard.



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