This is a very easy cake to make. A young person could make it with some parental guidance with the pineapple cutting and handling of the hot pan.
This cake is not as sickeningly sweet as some pineapple upside-down cakes and not as greasy because less butter and brown sugar are used to prepare the pan.
I use frozen cranberries or frozen pitted cherries instead of maraschino cherries, because I don't like the taste or artificial coloring of the maraschino cherries. But something red on the cake makes this one still look traditional.
You can use canned sliced pineapple instead of fresh, and vanilla bean paste instead of vanilla extract.