* Signed .exe works but has a cost.

* Unsigned .exe gets a security prompt to Run/Don't Run for the first time.

* MSI has an installation wizard.

* MSIX has a simple Install prompt like PWAs.

Are you saying I can distribute an unsigned MSI or MSIX without a SmartScreen warning? Are you sure about that? Others are saying the same thing, but I didn't think that was possible.

Can someone explain it you happen to know?

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.

Can you do the same on iOS?

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.

You missed the "without restrictions" part. You do not need to get the msi approved by Microsoft to distribute it.

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.

Not even close. MS is allowing the end user alternate means of installing software. Apple is trying to rob each iOS developer of 30% of their sales.