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There is a fellow in about a month, bringing a C30 from Portland to the sound. So if a 30'r can get from there to here, a 40'ish ft boat should be able to go south. Either coast, area can get bad winds and waves.
I am sure the Catilina's of that size have crossed oceans, even gone around the world. C27's have gone around!
A lot will depend upon you, as mentioned, looking at weather forcasts, if a hurricane or equal is near by, wait it out and make sure you do not sail into it! Local squalls, not a lot you can do about those, as they appear suddenly, ie cyclone twister thunder boomer style squals. Those you have to watch for yourself.
Personally I feel that there are some better designed boats for equal to a bit more money, but what youare looking at will work.