nbcman

Donor
What if the pirates are the main characters but we root for them as they still have a sense of honor. As in: don't hurt any hostages, always give a warning first, be polite and show respect
Robin Hood and his band of Merry Flying Men?

EDIT: Maybe use Mussolini as Prince John.
 
What if the pirates are the main characters but we root for them as they still have a sense of honor. As in: don't hurt any hostages, always give a warning first, be polite and show respect

Sure, in Pirates of the Caribbean we root for Jack Sparrow and Will Turner, not Commodore Norrington and Lord Becket.
 
This could work if you used an early version of a gunship working with the flying boat, and if close enough to a coast or island perhaps something like torpedo boats. The flying boat tracks down potential victims, calls in the gunship which proceeds to fire warning shots--the flying boat lands, and one member of the crew brings along a bomb strapped to his back, maybe, to guarantee cooperation, they loot and pillage, maybe taking a hostage or two for ransom, and then with the gunship flying threateningly about, retreat.
 

Puzzle

Donor
As opposed to seaplanes perhaps zeppelins using gas would work better. If the sky pirates move in at night it's quite possible that they wouldn't be detected against a dark sky while the ship's wakes would illuminate a trail for them. They'd come in to practically point blank range and just start dropping the most potent toxins they can find, send down a few crewmen to commandeer the ship and sail it somewhere where they can board it with more men. If they were careful picking their targets it might not be immediately noticed, and a zeppelin could move fast enough to avoid military vessels.
 
As opposed to seaplanes perhaps zeppelins using gas would work better. If the sky pirates move in at night it's quite possible that they wouldn't be detected against a dark sky while the ship's wakes would illuminate a trail for them. They'd come in to practically point blank range and just start dropping the most potent toxins they can find, send down a few crewmen to commandeer the ship and sail it somewhere where they can board it with more men. If they were careful picking their targets it might not be immediately noticed, and a zeppelin could move fast enough to avoid military vessels.
Zeppelin is too expensive to use for piracy. A Zeppelin costs more than a 15,000 ton freighter and very few companies in the world can make them. Anyone who can afford one, well no need to commit piracy if you have that kind of money

Edit: And gas? Do you want every to end up the #1 priority of every military on the planet, with instead of a chance a guaranteed death sentence waiting upon capture?
 
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The loss of ships to pirates airborne or otherwise will force up insurance and then affect trade in those areas. This will result in a strong government and naval response as happened a few years ago when Singapore and Malaysia responded to Lloyds branding the Malaca Strait a war zone.
 
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