I've tried to do a number of pirate runs yesterday and found them to be damn near impossible. Mostly owed to the fact that there's no small trade fleets around. Everything that flies can hurt you enough to take out at least one of your ships, which spells the end of a run if it happens early on. Compared to vanilla, your starting options are very generous and your relationship with the pirates is higher, but there's no good way to increase it through combat. All you can do is smuggle and slowly squirrel away points. In vanilla you may start low and with bad relations, but at least there's fleets you can tackle to improve the situation. Pirate privateer and raider are starting options, so they should at least be playable as such. Maybe 3 runs wasn't enough to get 'lucky', but in my opinion early fleet generation could use some tweaking.
I'm using SS+ plus all the companion mods, as well as a handful of compatible factions.