The best boat I ever had, when calculating fun vs. trouble/expense, was a 16' fiberglass open skiff with a 25 hp. Johnson. Got it in 1969 and fished rivers, lakes, bays and near Perdido pass until I practically wore the gel coat off the bottom from water friction. Since then, I've owned two 40' sportsfishermen (chartering) and a couple of Boston Whalers---had great times with all of them, but that little skiff was the best.
I am now the proud owner of a 12' aluminum Jon boat that leaks around the rivets, but that's OK because it never leaves the little fish pond.