Eh, you create a msi including all dependencies with tools provided to you by Microsoft free of charge and without restrictions. And mom gets a start menu icon.
If I don't think of cost as a fundamental issue, what differences would I see between either approach? They're both barriers to my intent and I'm not on board with the reasoning behind erecting those barriers.
It's an extra step in the process I only need to do on Windows, and the rationale behind it solely benefits Microsoft.
I'm not comparing Microsoft to Apple, I'm judging both of them against my intentions. Both companies throw up barriers to interfacing with their systems.