I've finally made the breakthrough - I used a bow while hidden to take out four of the pirates, leaving me, Lydia and my flame atronach to take out the remaining 2/3.
Honestly, the amount of work you have to do to get just a little bit of loot, eh?
There is a steam workshop mod that has higher bounty rewards. 500 gold for killing a bandit leader, 1000 for a giant and 5000 for a dragon. That way you aren't risking your ass for pocket change. I love the mods that are made. Most of them are well done.
One thing I'd love to see the next Elder Scrolls game do is where the entire world map is completely randomized every new game you create. Just like RPGs; Age of Empires, Starcraft, etc. No map is ever the same. I suppose that isn't possible with these games however. It would affect the story too much, etc. Too much for the PC to process.