Disclaimer, I don't own a Mac and I haven't used one in about 15 years.
First, the dpad issue is the same for me too on the Dualshock 4, however using the Xbox One controller both the analog stick and dpad work just fine. So if you want to use the dpad you'll probably have to find a program that can emulate XInput (Xbox) controllers or just use a Xbox controller.
Second, I've looked online about controller support with Wine and overall it seems support is poor. You might have some luck if you can manage to find the wrapper for AM2R and installing various programs to get it running, but again you'll also probably need a XInput emulator so... good luck? Honestly it's probably just easier to bootcamp Windows and play it that way but if you're fine with playing with the analog sticks that's probably the easiest option.
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