Then how aren't all the pirate ports decivilized within a couple cycles of play?
Personally, I've never felt the need to raid the pirate ports into the negatives, nevermind the continuous raiding needed to keep them there. Plenty of dosh available before you reach that point.
If they're all low on stability and you've a desperate need for cash, hitting large (major-faction) trade convoys in hyperspace is also very profitable, and doesn't exactly cost you much in the way of standing, either (if you keep your transponder off). I've gotten more than $1M wrecking a single supplies+heavy weapons convoy before, using nothing but a few destroyers and frigates.