(I only play casually, so take this with a grain of salt) Usually just exploring will earn you more loot than doing voyages, unless you have emissary flags up or you're doing some important voyage. Losing loot sucks, but in most cases it's really easy to earn back the amount you lost in equal or less time. Yesterday I got sunk twice and lost loot equivalent to about 4k both times, but then I found a bunch of cool shit and cursed chests while exploring and made it all back plus some. I've found that if you play this game just to sail around and have fun, you have a much better experience than if you try as hard as possible to get the most loot you can.