I generally do not use transports or trade but as a long term pirate faction player I can share my experiences from the other side with you, both my principles for pirating and my experience and what I do on an average day of pirating, when I go.
My principles: Firstly, I appreciate that this server is a roleplay server. Therefore, it brings me immense fun to play the role that I have as a corsair pilot and for the same reason piracy (for me) is not about credits or cargo, it is about (roleplay-) performance.
And what does this mean?
Perormance means that for me it is a bit like a stage performance, theatre or acting for a movie. I see piracy as an act of (roleplay-) performance and therefore I try to perform a good act.
At the same time I try to keep the fun of everyone else in mind. So how can I make piracy fun for not just me but also the one being pirated?
My solution: Because most people do not enjoy loosing a lot of their cargo or credits, I usually pirate only miniscule amounts of cargo or credits (fifty!! thousand!! credits!! ) or make a pure roleplay demand (like for example for.. furniture!) unless someone enjoys greater loss.
Some people are really awesome to roleplay with and we had super great fun rping with them on our shopping sprees piracy raids.
My experiences: Oh boy, those range from super horrible to super awesome. For example, I was once pirating with a few others and as we stopped a trader, he f1ed in space without a word. That was one of the bad experiences.
As for a neutral experience I once stopped a firefly transport in leeds with a cruise disruptor and asked for 500.000 credits! ... I waited... time went by... and.. suddenly he transferred 500.000 credits! And reactivated cruise engines. Not a word. But oh well
Awesome experiences are when for example we see a trader and stop them and he starts to interact with us and rp as if the situation was real and actually being worried over his cargo, his ship , his life, or his crew!. We rped super nice with him and ended up arranging further rp connected to food shipments to Crete or something and we stayed in touch with the player for a good while.
Summary: There are many ways to pirate and my own is only one way. There are a myriad of other, different approaches to piracy that are all completely valid and awesome I am sure.
If I get the impression someone does not enjoy pirate interaction at all, I try to be quick and perhaps find an rp reason to simply let them go (no cargo? nothing of use?). The most important part about piracy, for me, is to create fun and rp.
Creating rp is easy but creating fun is the hard part when you try to extort someone at gun point... but we love the challenge!