Sloop, Cutter or Ketch
I actually get to spend a fair amount of time on cutters. That seems to be the rig that I spend the most time helping people to sail as they seem to be less intuitive to non-performance oriented than some of the other rigs and of course I owned a cutter for 11 years, albeit one built in 1939 and have delivered several.
I have spent less time on ketches in recent years but spent a bunch of time on ketches when I lived in Savannah.
It is really from my experience sailing on boats with these rigs that I base my opinion. I will say that in rereading my comments i make no real mention of boat size and that is a mistake. As boats get larger divided rigs begin to make a lot more sense. As boats get up over 45 feet a lot could be said for a ketch rig. I still have almost no respect for cutter rigs as they are a bear to tack and their staysails are generally too large to serve as a decent storm jib and too small to serve as a decent 20to 30 knot sail.