With all due respect, experience may be "key", but aptitude is like being able to pick locks.
Just watched a video on two brothers who bought a 44' sailboat in Honolulu and sailed to Port Washington. A bit of rain, cloudy skies and near-windless conditions around the N. Pac. High, but nothing any reasonably intelligent person couldn't deal with.
This isn't a trip around Cape Horn!!!
After taking all this in, I've concluded that trawlers just aren't the right type of vessel for what I want to do. I want to travel long distances, - passages - and as has been opined, a motorsailer, or sailing cat will go farther, and possibly faster than a trawler, cost less to acquire, "feed" and maintain. We'll get to Hawaii, then Tahiti, or, if we buy a boat in the Med, cross the Atlantic, though the big ditch and then Tahiti and surrounds.
I'll gain experience as I go, but there is no doubt that I will make it - lots and lots of people do. I have a reasonable amount of sailing experience, understand the principles and safe practices and will practice in local waters first.
If you HAVE to ask "why", there is no point in asking "why" because you'll never understand. Some here get it, many don't. For them, green is good enough, but for me, blue will do!!!!
Fair winds, following seas, and to those who offered good advice on boat/engine choice, and boat-related advice such as stabilizers, my gratitude is yours. For those who felt they had to go into the weeds.... well we'll leave it at that.