When to go and how?
It's been said many times that if you wait 'till everything is perfect, you'll never go at all. That being said, one does have to be prepared and more importantly, to know the limits of yourselves and your craft. Some good reading of encouragement can be found in a recently published on-line article of Bill Teplow, who sailed his Potter 19, "Chubby" from Berkley marina to Hawaii in 24 days. Though blessed with an uneventful trip, the preparations he did may be of interest. Also many "smaller" craft have done repeated short trips on both oceans without incident ( look up "micro cruiser", Layden/Bolduc). In short go when YOU are ready, sail safely, but GO!!