Dawg, it is a matter of personal comfort level. The mythological "prudent mariner" probably is carrying an EPIRB these days, or at least a PLB. They've gotten dirt cheap in the last five years. The life raft...I'd like to see a raft OR some solid alternative plan but I can understand a greater reluctance not to invest five grand in a very disposable product. (They all rot and wind up costing serious bucks per year.)
Still, life rafts CAN be rented, and for 2000 offshore miles, "Don't worry be happy" just isn't my idea of the way to do things. I'd call it tempting the Fates, and those broads play to win.
Listen to your gut, if you don't like a situation, pass on it.