I've tried a few preliminary setting tweaks with Wine, but can't get past the run screen without crashing. Does anyone with more Wineskin experience than me (almost everyone) know how to get it to work?

No solution but I am in the same boat as you.

I've at least gotten to the character creation screen. Tested using Wineskin with Wine 2.1 and 2.6. Enable dsound using winetricks to get past the crash. There are two issues I'm trying to solve at the moment:

1) A very annoying video flicker (as in, it should come with an epileptic seizure warning)
2) Once you click on "create", the game asks you for a player name, however it doesn't accept any keyboard input other than left and right arrow keys. Neither Esc nor Enter works, so the game is stuck here.

Good news! It works now. I tested it in Wine-4.12.1 on a GNU/Linux box, but it should be the same under MacOS. I did have to disable d3d11 to get a decent framerate, but that may be because I'm using a laptop with an Intel video chip.