You can try to do it, loading each version into its own directory. However, I think the effort may well be doomed. The problem you are likely to face is that many Windows programs place files in the Common Files directory under Program Files, and they also place files in various directories in the Windows directory. These files are likely to be overwritten with newer versions of th file, if the newer file has the same name. The older versions of the program may not be able to utilize the newer files. Your only real option would be to try the VM thing to see how that may work.

You can try to do it, loading each version into its own directory. However, I think the effort may well be doomed. The problem you are likely to face is that many Windows programs place files in the Common Files directory under Program Files, and they also place files in various directories in the Windows directory. These files are likely to be overwritten with newer versions of th file, if the newer file has the same name. The older versions of the program may not be able to utilize the newer files. Your only real option would be to try the VM thing to see how that may work.