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make friends ( by hanging out and not endlessly sending friend invites) with some ppl and sail on their ships. That way you dont have to do repairs. I made a ton of money early on by sailing on my guildmasters' war galleon. She was an excellent sailor! We would come off that ship every time with over 800 gold. The high cargo hold makes for excellent pillaging and plundering on the War Galleons! If you are on your own... sail out from Cuba for some bigger ships.. if you have the PDF teleport.. there are always big ones out there. Stay away from the Bulwarks, Panthers and other lower ships.. they mostly have smaller amts of gold.
I guess it all depends on your skills on the guns and the wheel.
All in all.. best bet is being crew on someone elses' ship to start off.
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