Wineskin First Run
Unzip and move Wineskin Winery to your /Applications folder and open it.
The first time you run Wineskin Winery you will need to install an engine. Click the + button to add a new engine. To install the latest engine, select the top most item in the dropdown menu, it should say something like WS9Wine and then a version number. For the most stability, avoid any engine versions that have Staging appended to their name. Then click download and install.
Creating the app bundle
With the latest engine selected in the installed engine list, click Create New Blank Wrapper. Give the wrapper a meaningful name. Once the wrapper has been build, click View wrapper in Finder.
Next you will need to setup the wrapper. Control+click or right-click your newly created app bundle and select Show Package Contents and open Wineskin. This is where you configure the bundle and install your software. Click Choose Setup Executable and find your DiGiCo offline software installer file .exe file and choose the file.
Once the installation has finished, Wineskin will ask you which executable you want to run. In the drop down, select the one that matches your model of console, e.g. /SD11/SD11.exe and click OK.
While still in Wineskin Do a Test Run to verify the software has installed properly. If successful, the console offline software should open. In the System menu of the offline software, select Shutdown to finish the test.
Finally, exit Wineskin and navigate to your ~/Applications directory or wherever your Wineskin apps are installed and open the app using the mouse. If you app the app with the Cmd+down arrow hotkey, it will open the Wineskin utility.
If you are installing your software on High Sierra or later, there are two additional steps that need to be made before installing software.
First, in the Wineskin app found in your newly created wrapper, click Set Screen Options, uncheck Auto Detect GPU Info for Direct3D and check Use Mac Driver instead of X11. Click done.
Second, in the Wineskin app, click Advanced. Navigate to Tools > Utilities > Winetricks. Search for "video" and under settings, select "videomemorysize=1024" and click Run. If you get an error saying that the wrapper is still running, close the Winetricks dialogue and click utilities > Kill Wineskin Processes and confirm. Then go back into Winetricks and you should be able to change the setting.
Now, you should be able to click Install Software and follow the prompts.