Ok, copy/pasted the code you had at the end of your post into my terminal. No change. I tried updating XQuartz, used Homebrew to install Freetype, used Homebrew to install wine-devel, erased all my CoH files and Island Brew, restarted and redownloaded everything. Still get the green checkmark and then right back to Ready to Play. Below is the latest Island Rum log:
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(EDIT: Minor quibble for style points. I "Spoiler'd" the output of your log, the content isn't lost. You can also upload a text file in the future. --GM Tahquitz)
Thanks for any help you can offer!