Wine version (via wineskin winery)
Steam Retail - includes latest patch and High Resolution Mod.
Every thing runs fine, I get the smashscreen, but when I hit play my screen flickers a few times and than I get the error `error initalizing video mode 1024x768`
That's a bit of an older Wine engine, but Wineskin itself has issues with High Sierra. For crashing you need to disable Auto-detect GPU
in the Screen Options of Wineskin.
It almost sounds like you are past that though. I did read a comment that which said, "However with OSX 10.13 the Intel GPU does not report a vendor ID." In which case Wine itself may not be seeing your GPU correctly. You can override that, basic system info would be useful, but see if disabling Auto-detect GPU works first.
Playing around with screen options didn't do anything, and I'm not sure what winetrick could fix this (if at all). Is there anything I can tweak to make this work?
I guess you could try with X11 driver instead of the Mac driver.