I'm earnestly surprised that the compatibility efforts GOG has went through on so many titles hasn't made playing most, if not all, of those old titles playable through WINE. So many of the old DirectDraw / legacy DirectX games have been made capable to play by translating to DirectX 9 that I would imagine WINE would work swimmingly in those cases. I imagine though that you've put in the legwork to try and get those to work though, so I trust your experience, but my surprise remains all the same.