High School Master and Red Sakura Mansion share the same engine: Tyranobuilder. This post may be useful to you, I did what suggested and I managed to launch the game (tested on Ubuntu 22.04 + wine 8).
Thanks again for the tip, unfortunately that didn't alter my results. I'm suspecting now it's something on the package level, a package missing or perhaps too new of a package maybe even but I don't know for sure and the messages it gives me really isn't providing me a lot of help finding the answer.
Japanese language shit and use winecfg to set the windows version to vista
rolling back windows helps with a lot of shit under wine, because the programs will use older better supported APIs when they think it's an old windows version, instead of the newer ones that cause wine to flake out