This post stems from a conversation started over at the SHP Facebook group https://www.facebook.com/groups/SierraHelpPages/permalink/1496139430625909/
My thanks to everyone there, especially Derek Wood for giving me the rundown on getting this up and running.
It should also be noted, I've got GK III running using these same instructions.
Finally, this post assumes you've purchased your games from GOG and are using their installer. While I'm sure the process is similar for the original releases, the GOG installer streamlines the process, and was all I had on hand at the time.
Step One: Download the latest version of Wineskin Winery - http://wineskin.urgesoftware.com/tiki-i ... =Downloads
Step Two: Once you've moved Wineskin Winery to your Apps folder launch the application. From the main menu click the small + button next to "New Engine(s) Available". You will be presented with a new dialogue box from which you want to search for "WS9Wine1.7.0X Engine" and click Download and Install.
Once the file is downloaded you'll be returned to the main Wineskin Winery menu.
Step Three: Click "Create a New Blank Wrapper" and name it "Quest For Glory V". It's going to prompt you to install some additional materials (Mono, and Gecko) but you don't need them, just hit cancel. Wineskin will now do it's thing to make you a wrapper.
Step Four: When prompted, click "View Wrapper in Finder". You will now see your newly created wrapper. Right-click and select "Show Package Contents".
Step Five: Double click "Wineskin", and then click on Install Software. From the new window click: Choose Setup Executable
Step Six: Navigate to your GOG installer (in this case: "setup_quest_for_glory_pack_18.104.22.168"). Wineskin will then launch the installer. Since you only want to install Quest For Glory V, click the options button, and uncheck everything other than "Quest For Glory 5". Tick the box stating you've read the EULA and click install. Once installer finishes it should prompt you to launch the game.
You will notice that unfortunately the opening videos won't play (you'll have audio but no picture). So far we're not sure of a workaround, but you can just skip these and get to the main screen. You can now play to your hearts content!
When you quit for the first time Wineskin will ask you to pick an executable for the next time you launch. Stick with the default.
That's about it! Good luck, and happy gaming.