At 74 years old, I've been boating ever since I was a young kid. I, however, have never crossed an ocean in anything smaller than an aircraft carrier.
On that carrier (Enterprise) we did experience seas of 25 ft, off Cape Hatteras, which pretty much convinced me that crossing an ocean in anything smaller than CVN 65 was out of the question.
I don't know if I admire people who do it or if I question their good judgement. I do know that when I hear of people that have done a major crossing, I marvel at their tenacity. (being it ill advised or otherwise.)
Coastal cruising has been and still is my favorite part of boating. To be sure, you must pick your weather window but in my opinion it is much more interesting than chugging along for days on end on a featureless, endless ocean passage.
P.S. If someone held a gun at my head and forced me to cross an ocean, I hope it's on a 65' Fleming.