OK, thanks for the info. I will look into this. Do you have Gatekeeper or any sort of anti-malware that might interfere? I heard one Mac user had to set Gatekeeper to allow apps to start from anywhere (temporarily) or it wouldn't load.
You may also want to try this:
There is a problem in Wineskin GPU detection code with High Sierra changes.
By default your wrappers may crash or fail to launch.
Currently you can work around this by launching Wineskin.app, going to Set Screen Options, and uncheck the Auto Detect GPU for Direct 3D option, and the wrapper should work normally.
http://wineskin.urgesoftware.com/tiki-view_blog_post.php?postId=87