Since it took me so long to figure out the way to get this to work with little to no updated information or guides, I've decided to write this guide on getting School Days HQ running on the latest version of Crossover. I personally used macOS 12 for this but I'm sure this will apply to all platforms. This guide is based on me spending countless hours trying to figure out how to install all dependencies required for the game. If you have any problems, leave a comment and I'll try to help you out the best I can. However please make sure you have read the guide THROUGHLY before leaving a comment.
WHAT YOU NEED
Crossover (whichever latest version is available)
School Days HQ (1.00 & 1.02 works)
Windows Media Codecs (required to prevent crashing after starting/loading game)
Visual C++ 2010 Redistributable Package
MSXML 4.0 (might be optional, but better save than sorry)
SETUP
Create a new bottle and name it accordingly. Make sure to set the bottle type to Windows XP (32-bit)
Once the bottle is create and running, click install and search for Visual C++ 2010 and install it into your bottle.
The Visual C++ installer should automatically open and you can proceed with it as normal. Once the installation is complete, go back and search for MSXML 4.0. It should also open automatically.
You will come across this screen before the program beings to install MSXML. You can most likely type in any name but I chose to stick with the default username (crossover).
Once all programs are installed, you are going to download the Windows Media Codecs. The game heavily relies on codecs from Windows Media Player to function, as the story is told through video cutscenes. Since it is next to impossible to install the required version of Media Player in Crossover, installing the codecs are the next best thing. Failure to install the codecs will result in the program crashing when attempting to load a cutscene. Visit the Windows Media Codecs website and scroll down to the bottom of the page, where you will see Windows Media Format Runtime for Windows XP/Vista
Download the installer and click Run Command in Crossover, click browse and select the installer file and click Run.
Go through the installer. In most cases it should succeed with the installation, however in the case it does fail, quit the installer and run it again.
After the codecs are installed, go back to the Run Command Window, click browse and select the installer file for School Days.
After a few seconds, you should be taken to a fullscreen installer for the game. If everything was installed correctly, you should be able to go through the setup with default settings and no prompts.
Once the installer is finished, you can start the game and enjoy School Days. :)