I've only just begun and so far have just been clearing the docks of thieves. I haven't messed with the pirates yet. When it comes to henchman, do you have to pay to hire them one time or every time you need them? If I have to shell out 200-300 gold a half dozen times in the game, I'd rather wait for awhile.

Anyway, so far so good.

You just have to pay them one time. But if your character has a high charisma, then you can persuade them to charge less. And if your character is an Elf then you can persuade Linu to charge just 150 or even 100 gp.