Hmm - interesting discussion here. Let me point out something if I may. The rules for pirates seem to be more restrictive than rules for any other player.
Steps for a pirate to follow while engaging other players:
1. Be in a system you are allowed to pirate in - for a Rogue this means I must be in Liberty or independent systems
2. When (and if) you find a target, check to make sure they are above level 30
3. Get close enough to scan for their ID and verify they have cargo in their holds
4a. If their ID is one you can pirate and they have cargo, start taking down their shields and hull (or you can demand before you open fire)
4b. If they have no cargo or an ID you cannot pirate, gotta let em go
5. Demand cash or loot before they are destroyed
6a. If they decline to pay, kill them
6b. If they pay, receive payment and let them go about their business
7. If they dock, sell their cargo and undock empty, gotta let em go
Now typically what happens is the target will either dock, sell cargo and undock or they'll dock and switch to a different character. The latter tends to piss me off. I can't camp and attack when they undock, but I can wait around the dock and follow them (giving them some time to maneuver) and then re-engage. And its becoming a bit more difficult to kill Trains these days since they are typically wearing Armor Upgrade Mk VIII (which I'm pretty sure is not permitted). And they will typically have weapons you'd expect on a battleship, not a Train. I even got attacked by two Trains once. They tore through my shields and armor like a hot knife through butter. Which brings up another problem with pirating these days. The rules say I've gotta be in a gunboat or smaller. If a trader is gonna be heavily armed, I'm gonna need help or be in a bigger ship.
A trader is RARELY pirated successfully these days simply because the rules for pirates are extreme and the traders tend to hang around NY or heavily protected systems such as Texas, New Berlin, Cambridge or New Tokyo. I try to pirate a ship in New Tokyo with my Blood Dragon and KNF is all over me. I make an attempt to pirate in Texas with my Rogues and SA is everywhere. I make an attempt to engage a trader in Omega 5 or New Berlin with my Red Hessian and SF or RM are there. Traders have no challenge on this server. Since I've been on this server, I think I've successfully pirated a total of 5 traders. I see more action from RM, SF, SA and KNF attacking me on sight than I do from traders. I'm glad they get the opportunity to RP their characters to the maximum extent possible.