Proas were in the Challenge in about every year except current event. We had Raptor this year. which is, arguably, tacking proa.

It is quite typical for Proa to fail apart just after Tampa Bay.
Very few made to checkpoint 1.
There was one homebuilt tacking single outrigger which made to the finish in 2003. I believe they pull ashore and place outrigger on lee side every time they needed to tack. <img src="http://www.catsailor.com/forums/images/graemlins/smile.gif" alt="" />

There are many obstacles on the course; however it is do-able by catamaran. Prior to spectacular performance of Tornado, trip was completed on G-cat 18, Hobie Cat 16, wooden A-cat, inflatable cat in different years