Hi David Brooks!  - definitely wanting to tackle this and ensure you get an answer. 

Unfortunately, the platform doesn't have anything OTB that would automate this service flow. I could see a lot of variables that you would need to account for. I suspect in the long run it might not be worth the payoff of trying to automate/interpret the users' system and serve the correct file.

I would suggest a bit of an old-school UX method of having different avenues to collect the content or very clear documentation/signage that helps poke the user to choose the content needed.  The best example is actually at the bottom of this page. The Downloads column has direct access to the file type based on the user's system of choice. Another great example would be the Android/Apple buttons at the bottom of the default Igloos.

Thank you. Meaning if I had the Igloo deskop client installed, then went to a doc library on our intranet page and attempted to download an OFT file it would auto download a Mac compatible format?