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I think you should talk to your professor and get some guidance. General window management is a big topic, its more of an OS topic than a language topic.
For example, your question about being able to read the name of an .exe file, execute it and display the user interface of the .exe program is a huge issue, and very OS dependant. If you are working on OS-X or Linux, you don't even typically use the extension name of .exe
When a Windows program runs, it assumes that it has the usual Windows windowing system available, so it can just call the usual Windows API function to say open a dialog box. If you ran that same file on OS-X or Linux, you would not have the Windows API.
I may be not understanding you, but what you describe sounds more like a team project for graduate students, not a one term undergrad project
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