To be honest, I really don't like the personality that pirating gets on these forums.
The mechanics of a game are in a sad, sad state when a pirate actually bothers to come here and outline instructions on "how to get pirated", which so many of these threads boil down to. Most of what I refer to with this are the mechanical workarounds and "codes of honor" that are more or less based upon those.
Someone after your cargo should get stolen goods, period. They are, after all, stolen, whether they where extorted or outright taken. There should not be a way to circumvent the bounty system. This whole "stop so we can have a tea part, and by the way also I take your stuff with no consequences" concept is, uh, pretty lame.
A mechanical way to do this is simply to have any goods picked up be stolen.....you know, the way ALL other goods in the game are, even if you hop into a spot with no ship in it. An even better way would be to "signature" every single piece of cargo in the game, and any living ship retains its signature, and it lingers on the cargo if that ship is destroyed by something else. This opens the door for all the other cargo floating around out there to be marked as salvage and open up another actual, legitimate profession when a person runs across actual space salvage, which is out there everywhere anyway.
Note that this would not, in any way, prevent a player from dropping cargo to appease a pirate and attempt to buy their life. It would simply remove the mechanical workaround in place to let that pirate be unidentifiable as such due to his lack of bounty, which brings up...bounties.
Why on earth can you pirate in a clipper, mash a sidewinder into a wall, then pirate away in a clipper again? I disagree about cancelling insurance, this is an in game concept created to make the games death penalty the level desired within the game and isn't centered around any particular facet of a reality.
A bounty gained in one ship should really not be clearable by being destroyed in a cheaper ship, and certainly no bounty worth more than the ship(or the ships rebuy, at least) should be clearable in this manner. It creates a system without consequence, and promotes yet another system of working around game mechanics(you don't try to not die, you try to not die in your expensive pirating ship but have every intention of dying in a cheaper one if the heat is more than you can handle). If you're meeting a pirate that suggests that "it's a hard profession", they should probably be in a sidewinder, not in a pimped out anaconda or Fer-De-Lance, which makes about as much sense as the guy riding in the back of a Rolls Royce claiming he makes a meager living(and yes, I know you can earn the money in one profession then use the ship in another, that's quite beside the point).
A pirate with an illegal load of cargo and a price on his head should have to be discreet to enter regulated stations. Part of the skillset, and ship choice, should include the planning aspect related to getting that stuff in to be sold without being caught.
And with that, smuggling should be given a long, hard look. It's silly that a person with illegal slaves or battle weapons has to sell them low on the black market in a system in which they are prohibited. Stuff like this should be worth a fortune in these systems, it's only logical. Stolen "normal" wares may be worth a touch less, and a stolen tonne container of turds should probably be just plain useless, because seriously.....just, yeah. Similarly, in a system that is starving, stolen food might fetch a handsome price but in a system that isn't directly short on food, people probably shouldn't be interested in contraband pop-tarts. A little logic on the black market prices would really have to be set(and should be anyway), since this is yet another reason that a pirate will want to circumvent the mechanic of his stolen goods actually being stolen.
Incidentally, if you're a pirate and into the idea of attempting a peaceful resolution to mugging people(regardless of whether or not you agree with anything else), when you catch wind of someone that prefers to shoot first it's probably worth your time to hand them a few rebuys. Like, enough rebuys that they leave the system. Nobody in their right mind kills the engines and waits to see if the other guy is hostile in an open PvP internet environment because the odds that he's a chatty Kathy rather than a deranged psychopath are pretty small. Those guys are pretty much guaranteeing that there is no real reason for a person to try peaceful first, and anybody that has ever seen open world PvP on the internet knows that.