Sailing is the worst aspect of the game imo. Help me out.

[Diego Birmingham]

Sounds like you're not sailing very effectively. I rarely crew up anymore on land or sea since my guildies and I mostly have finished the Boss Battle. I've had a war galleon for only a short time but LOVE it. I can take on any ship one on one and usually sink them. I'm bringing in 200-400 gold consistently with a full hold and only 1 point invested in treasure sense. My broadsides are maxed, but I can't remember the last time a shot a cannon.

I suggest some practice. Learn maneuver & strategy on "easy" targets--bulwarks & panthers mostly but don't be afraid to take on more challenging targets. Use Bartholomew Watkins quests to earn extra gold while sailing in case you get sunk. You'll only have to make up a small amount of gold out of pocket to repair from a sinking. Most times you'll make a profit as the WG is one tough ship.