You can do anything with a cat. It is a matter of proper planning and money.

People have crossed from the Horn to Antartida on a beefed-up Hobie 21SC. But they started preparations a year before, built it in foam sandwich (unsinkable), had a support vessel, land crew, cameramen, 3 personal epirbs (one for the boat and one for each crew), 2 satphones, VHF, waited for the right weather window, etc.

Bermuda is not nearly as difficult, so maybe you don't need the cameramen :-)

If your friend likes the R33, have him call the factory and ask for a beefed-up version with smaller sailplan, chicken float and self-righting system. If they make it, then go on planning.

Good luck,