Thank you, goobdoob for sharing your installation guide of Man of the House! But there is a major difference between MotH and Timestamps regarding animations/videos:
Dear Wine users, animations
do not work with Wine! Doesn't matter if you are using Wine-Staging/Wine-Stable on a Mac or Linux! The reason for this is: Windows Media Foundation!
The native Windows version of the game needs Windows Media Foundation for animation playback. However, Wine so far, is not able to use all .dll's of Windows Media Pack or other .msu packs.
Anyway, above installation guide will make the game run on a Mac, but without the animations! (Some animations are important to understand the story a little bit better, because they are more as just some sex scenes. Keep this in mind!)
If you want to enjoy the game completely, and not just the renders, than you need to install a Virtual Machine with Windows. This is the only solution so far!
Thank you for reading!