If I were a pirate leader, I'd just read shipping logs and have a few people giving me intelligence for money. Not even necessarilly letting them know what the intelligence was for. Let 'em think it was industrial spying. Even a half-@$$ periphery world will have due times and cargos availalbe beforehand. It's too expensive to just jump into a system and try to sell stuff to the locals, most of it should be bought by on-planet business ahead of time.
You are correct, if every two-bit periphery world has an HPG. Otherwise, news only travels as quickly as the jumpship. The jumpship does not make money selling stuff to the locals. It makes money by carrying droppers and has no real concern with what the droppers are carrying. In fact, it is better for the JS if it does not ask, let alone know, what the droppers are carrying, that way, there is no blame for the JS that brings a less well-heeled pirates' dropship into a system for a raid (Jumpships are rare and it is really important for the Powers That Be that those operating the jumpships are able to keep them in spares, that and plausible deniability is a Good Thing for covert ops). A jumpship can earn some extra money running low tonnage/ high value goods and contraband, but the local crime boss/pirate leader is the guy paying for shipping, so only a rival is going to try to raid that cargo and the JS crew has already been paid to dump it overboard at the recharge station.
Peripheral interstellar trading is accomplished by the local chartered DS going to the recharge station and hooking up to a docking collar. Once the dropper gets to the source world, the trade factor buys stuff. After loading, the DS hooks up to a docking collar likely to bring it closer to the destination. A pirate at the back-end-of-nowhere peripheral world might know what the factor was hoping to buy, but will only know the cargo manifest if someone sends that information on ahead and can only know the arrival time after the DS figures it out (trade in the periphery is carried by JS hopping between systems, on spec that there will be DS waiting for transport and a world that does not have waiting DS frequently enough risks being abandoned).
Pirates have to be very picky about what high-value stuff they sieze, as the people that paid for it will either hire mercenaries to protect it next time, or they will stop ordering it. Successful pirates have to keep from killing the goose that lays golden eggs. Fencing the stuff is a problem, as it will have to be sent to another system that will pay for it-- the locals will know that the goods are stolen; unless, the pirates only take a small enough percentage for a fence to hide the stolen goods among the goods that made it through.
Along with the peglegs, hooks and parrots, we also have this romantic notion that pirates siezed gold and jewels. Pirates purchased gold and jewels to keep their wealth portable, but any vessel likely to have any amount of gold, jewelry, or just great stacks of silver coinage was a warship that outgunned any pirate vessel and might carry enough marines to take a pirate haven by storm. Pirates, unlike privateers with a letter of marque, had only such cannon as they could scrounge, and only a privateer gambling to grab a spanish treasure ship would spend the money to hire the guns and gunners needed to take on a warship and would be quickly bankrupted if he missed a prize. The likeliest goods fenced by pirates of old were liquor, finished metal goods (mostly nails and horseshoes), and ships, with the ships having the highest value. In the BTU, JS are hard to sell, as they can only be serviced at a few locations, and a JS with all the serial numbers filed off is obviously stolen. High valued goods that a pirate could fence anywhere are rare. About the only commodities that really qualify are battlemechs and dropships (an unscrupulous operator of a JS could make serious coin dropping small mercenary bands where they get ambushed by pirates. As the dropper is hooked into the collar, modules are hooked into the dropper's sensors to keep them happy and blind long enough for the JS to pull away. To prevent hard feelings, a different JS shows up to take the victor of the ensuing combat and his spoils to a fence.)