I haven't really seen an ugly boat posted here, yet.
Somebody has to set the bar:
RAW FAITH
was one ugly boat. So poorly conceived and built by an epic narcissist, she was rescued a couple times by the CG after leaving the port of Rockland Maine.
She was put under house arrest to stay in the harbor until she could complete one tack, under her own power...
Finally, on a windy day, she was able to jibe going downwind (I think). That free'd her (CG was so tired of babysitting the boat), and she headed down the coast.
She sunk a few hundred miles downwind. The captain and crew were rescued, for the last time.
RIP, poor tub.