After playing as other kinds of characters I finally thought I'd try to go pirating.
I hoped that would give me much more interaction with other players.
But so far it has been lots of boring waiting, boring chasing, and getting chased off by bigger badder ships.
What's the secret to making pirating fun?
It is a factor you really cannot control, an enjoyable pirate encounter depends on both the victim and the pirate's RP. You can have a very good RP story for your pirate but the victim might not, or he/she simply does not try to RP.
Try RP'ing with other pirates and working in groups.
Unfortunately, pirating is only as fun as the associated trade routes. I'd say pick a high-profit one and a good place to set camp, then wait for them to reel in.
Oh, and get a partner. Pirating is always best in groups.