When I apprenticed in the bakery, we made a ‘whip cream bomb". It was layers of chocolate cake, layered with strawberries, bananas and whip cream. We would stack it the same way one would do the ’naked wedding cake’.
We used a strip of plastic film, (not sure if it was actually plastic) but we would wrap that around the sides of the cake)
In response to your questions: We would just cut the layers in half, not bake individual cakes. If you are afraid of it drying out, I would brush the sides with a small amount of simple syrup. I would be very careful to not make the outsides of the cake soggy.
In order to insure the cake not dry out, you might be able to wrap the sides carefully (as not to mess up any fillings) with wax paper until you set up the cakes.
Hope that helps.