Both Flying a hull and trapping single handed are "just go for it things"
With the trapping just raise your wires a bit. And I don't mean so high that it looks like you are standing on the rail!!! Just enough to make getting out easier, then as you imprve your technique you can lower the trap to the proper height.
I have been sailing a 16 for about 30 yrs (ok matt, billy, etc i know I'm old) I learned to trap single handing by tying the end of the mainsheet to my trap harness. Today most boats have a continous traveler/mainsheet line so I wouldn't hesitate to tie a tether line or something like it.
Remember if you fly high enough you will occasionally flip, All part of the game!!
On righting a 16 single handed I have used both a righting bag and a shroud extender and found the bag the best option.
Remember there are two kinds of cat sailors... Those who have jumped of the boat (unhooked) and those who WILL jump off the boat.
