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Using a drive with permissions between two machines will present some issues. Permissions are associated with users, typically the owners, of the file.
Do you have the same exact user setup on both machines? Unless you are using some system to share account data across all of your machines, your permissions may be worthless.
Windows has UIDs tied to permissions. If I were to have a file owned by Boner on one Windows machine, and were to move that file to a second machine, the second machine probably wouldn't understand the UID assigned to that file since it will be a big hairly Windows UID instead of a username. Add MacOS into this, and I think you'll have quite a challenge getting security information on the drive to work seemlessly across your machines.
You might look into something like PGP to encrypt instead.
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