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I think you would be better off trying the VirtualBox (virtual machine) approach. Although I have no experience with it (as I have no Macs) I've heard you can pass through the USB device in raw mode a get it to work.
I agree with Paul's advice. If you can run Windows in a VM we're hearing that works well. But ValiDrive digs deeply into Windows to manage its very low level USB operations and WINE (on Linux and presumably Mac) doesn't emulate Windows enough for ValiDrive. :-(
I'm afraid there's zero chance for v1.x. ValiDrive v1.x uses aspects of Windows' USB support that have not been emulated under WINE. There's some chance that I could make v2.x work under WINE by using a different drive selection system. It is on my list to explore once I revisit ValiDrive after SpinRite v6.1 is finished.