One of the things I noticed working on Mac is how few "extra steps" are needed. I picked up a Windows laptop the other day and naturally started setting it up for building with Allegro and dgaf about anything else. Anyway, all these extra steps to add the PATH, use this terminal for A, use that terminal for B. The Windows UX is not very nice either, (partly from a lack of familiarity), but I've already run into a few annoying bugs with windows permissions screens.
I would find it frustrating to spend a lot of time in there. For my concerns, I intend to drive most of my development with Mac, and have some communication protocol that drives builds and runs tests on the Windows platform.
So far I've had to install MinGW through some installer I downloaded from the internet, and also Cmake as well. It feels sloppy and vulnerable to adware. With Mac it's literally brew install allegro and it works (assuming you have brew which is just an equally easy terminal command). Building from source is really easy too, which is what I'm doing now so I can be at edge.