What kind of technology would a dragon-like species have during the golden age of piracy?

Question

The world I'm working on contains multiple "sub-species" of sentient, European style dragons. When standing on all fours, a human comes up to your typical dragon's shoulders, and they are quadrupedal with opposable thumbs, with four legs and two or four wings, and can reasonably be expected to remain in the air for at least several hours at a time (and that's the low limit for sick or malnourished dragons).

Some dragon species can breathe fire, but no dragon species has inherent fire resistance. There are a few other 'inherent' abilities like ice breath, a venomous tail stinger, breathing underwater, and silk-weaving. Also, some of them have 'superpowers' of sorts that are not normal for their sub-species, such as super-hot scales, telepathy, or the ability to communicate with plants due to circumstances of birth or genetics.

Now that all that is established, let's establish the setting. It's set in a series of scattered islands. Travel between islands without a boat is possible but incredibly risky unless you can breathe underwater, as it's hard to judge distances between islands and easy to get lost out at sea without landmarks. Trade is really important, and piracy abounds.

What technology would these dragons have? What would their boats, sea tactics, and weapons look like? In case you need to know, they're currently in black-powder age technology; firearms do exist but take a long time to reload and are prone to malfunction.

Answer 1

Navigational Technology: Compass, Sextant, Clock, Charts, Logs

• In a situation where "Trade is really important," the natural inclination of a ship owner will be to reduce their risks and increase the likelihood that the ship will return. The ability to determine position and navigate after a storm or a battle is a key skill that reduces risks.
• Logged information permits data-sharing among merchants to identify avoidable pirate hot-zones.

Defense Technology: Signal mirrors, air-dropped bombs, poisons

• Dragons seem naturally-equipped already for melee-style fights. They don't really need early firearms when they can fly and have ice-breath and stingers.
• Piracy isn't really about the fight anyway, though that is the fun part to tell a story about. Piracy is a business -- it's about selling (or hostaging) the booty/crew to make a living. Pirates tend to be risk-averse, like everybody else. They will pass by a seemingly-strongly-defended boat for an easier target.
• A strong defense includes lookouts aloft, communicating with their ship using their signal mirrors.
• A strong defense also includes air-droppable bombs to destroy the pirate ship (if any). They don't need to be gunpowder bombs -- any kind of incendiary and ignition source will work against a wooden ship, like a bottle of alcohol and pitch and a burning rag.
• If you have clocks and gunpowder, your merchants can create a self-destruct (deadman) bomb to sink/burn the ship in the event of capture. Even if the pirates win the battle for the ship, without the booty they lose.
• With poisons and clockwork bombs, merchants can have a bit of their own fun against aggressive pirates: They can offer to buy safe passage from the pirates, but the goods are poisoned (if carried away by air) and/or planted with fire-bombs (if carried away by ship)

Answer 2

I imagine that for the fire-breathing sub-species, the gunpowder might be lit through the use of a bit of flame-breath. However, this could lead to accidents where the firearm's gunpowder compartment explodes in their face.

Answer 3

What they buy from humans.

The dragons were very impressed with human tech when they encountered it. Dragon minds do not work that way; they are not creative or inventive like humans. Dragon tech is almost all either purchased, stolen or copied from humans.

This offers grist for the story telling mill because as opposed to describing new dragon tech you can describe the dragons trying to deal with familiar tech. Rich dragons might commission custom items but many dragons will have human sized tech which is a poor fit for them and can be hard for them to use.

There is an occasional character referred to as Clever D (aka Clev) because she is a dragon who can think like a human; she modifies human tech to work better for the dragons and occasionally comes up with improvements that are new to dragons and humans alike. She goes from island to island on a little 2-hulled catamaran that is the fastest boat on the water; neither human nor dragon can figure out its secret and she is not telling.