I see only 2 problems,both from improper preparation when it was painted. It was origionaly natural finish,varnish or polyurathane which was not cleaned and primed before painting. The joint between top and trim was caulked or has too many coats of paint. I see nothing structuraly wrong with the piece.

Thank you so much for the advice, klem1!

Defects in distressing are usually deliberate, and meant to look that way. When reading that something is distressed, it's totally up in the air, as every manufacturer or custom painter has their own idea of this treatment. There are no tried or true rules.