go for it
I took my 14' Aire and remained upright, but I took conservative lines. Other boats on our trip, both 14' and 16', flipped. Luck of the draw - flips just kind of happen down there, usually very quickly! The smaller boats are definitely easier to flip back over when it does happen.
I preferred the comfort level of rowing my own boat over a bigger boat with which I was not familiar. But on the other hand, it would be kind of nice to have everything there waiting for you too with a rent-a-boat. It was a long haul from Oregon, let alone New York!
Show me your OOOOOO face