Windy is a handy wind forecast tool. There's a YT of a light twin pilot using it to time when to fly to California from Hawaii.
The NTSB initial report shows no flight plan filed. On a flight plan (legally required) the paperwork and possibility of fines is much reduced if you have to declare an emergency and make a fuel stop once it looks uncertain you will make it all the way. In any case, much less trouble than swimming.
Halfway, or even earlier, into the flight is a good time to check if fuel is looking good. Given the headwind, he would have had a nice tailwind and no paperwork if he had turned back to Alaska, just an extra fuel bill.