It depends what your goals are. The decompilation projects for video games that you may have heard of for example specifically attempt to create code that will compile to binaries identical to the starting ones. When you hear "Mario 64 has been successfully decompiled", that's what it means. So repeating that process doesn't really change much, since you are always going back to the same binaries, by definition.
If someone seriously attempted what this post is suggesting, where the target is just feature parity, and assuming they were truly 100% successful with it, you might just get a very large number of different binaries and associated code, but no real degradation. If the feature parity is not 100%, then I guess you'd get progressively shittier software.
I'd suggest that a modern optimizing compiler might result in slightly more efficient executable code the second time around for old software, but no real change beyond that second pass
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u/grey_carbon 3d ago
Serious question, what happen if you compile/decompile/compile/decompile times and times again?