In other words, the plot of Hidamari Sketch, the anime adaptation of the manga by Ume Aoki that premiered on BS-i ten years ago.
The original series was followed by three sequel series and a handful of OVA episodes, all of them with the gentle, whimsical humor of the original.
The plot boils down to “gently eccentric high school students boarding in a gently eccentric apartment building study art at a gently eccentric school.”
A lot of it is character-based humor: a person will like the jokes as much as they like the characters.