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The first thing I would do is try selecting several different download regions, some close by, some far away (a different country.) I would avoid using a VPN with Steam.
Worst case scenario, you could use SteamCMD to download the OS X version of the game on your Windows PC.
https://developer.valvesoftware.com/wiki/SteamCMD#Cross-Platform_Installation
Maybe that one works for you?
Yes you can transfer the games over, that works as well.
You'll also probably hit an issue in that you need to launch the game in online mode at least once from the mac before you can run them in offline mode while not connected.
That's a good idea, however it doesn't work at all, home or at school, has a filter that blocks it 24/7