Don't accept a quest without a full energy bar, because your chances of not finishing the mission will increase if you accept with less-than-full energy.
Get an easy Man o' War by capturing a colony, then manning the ship and waiting for an attack on your colony. Stay close but don't enter the battle until daytime. There won't always be an MoW but try this a few times (save the game just before you go into battle, and keep reloading from that save point if necessary). Sometimes you will even have TWO MoWs invading your colony.
Wait until your cannons severely weaken the attackers, then board the ship. You need sufficient crew to man one of these beasts, but this is as easy a way as any to get a Man o' War.
Also, the most important thing to your ship and your crew is SPEED. Go for speed above all else - try to upgrade to the fastest ship possible for the purposes you need, and don't plate your ship unless you absolutely have to. Upgrade to the fastest sails possible. And use only one type of ammo, to not only open up more space for booty, but to lighten the load and thus increase speed.
For a cheap and easy way to raise morale, go to a tavern and go to the crew hire menu. Look at the average morale. If it's higher than the average morale, fire only a portion of your crew and then rehire from the pool and your morale level will go up.
For a high-range weapon that lets you strike from afar, use culverins. Hit without being hit.
I hope these help! Got anymore hints? Post them!
