Solid simple premise delivered beautifully. The story feels a little close to home. My grandma is a lovely woman who came from a very poor family. She likes to tell me how her childhood used to be. How she and her siblings had to work hard, eat whatever they had on the table, etc. Always feels like a lecture session, but it never bores me because she's always so passionate about telling me her stories. And that's what I like about WMTW. The father lecturing his son all the way felt grounded and authentic, making the scene very sentimental. But, this is a visual novel. I'm afraid that scene was "too much telling, less showing." The scene between the siblings (albeit short) was sweet, arguably the most visually appealing part, I wish there were more like this part.
On the technical side, I love how you contrast the art style between the past and the present. However, I personally like your 2D style better. The 3D style felt a bit off, perhaps because my brain expects 3D objects to interact with each other, having depth of field and lighting interactions between them. But this is a purely subjective preference.
The animation for the main menu looks appealing and communicates well what the readers could expect from the story. A little tip: Ren'py can do frame-by-frame animation just fine, you don't need additional video editing tools at all.
Lastly, this is perhaps my biggest grip. I feel strongly conflicted about the NSFW part of the story. I don't think that part adds significant value to the storytelling. Instead, it retracts the mood that has been slowly built up. Perhaps you felt the urge to include it because you wanted to make the project fit within the boundary of the theme with that one line. Perhaps it's purely to showcase your main project.
Regardless, WMTM is a pleasing short read that hits its mark.