I've always found GMG to be the iconic representation of the "grey area" and probably only holds it's lawful status due to the political power of H-fuel, that there are lines they wouldn't cross, and contrary to common belief, are highly organized and quite capable of defending itself from invaders. But they hold some mighty grudges and the infocards are quite clear about their hostile view against those they hold a grudge against
But as to my above post, having read it from here I should add that I have done the run a couple times now and I haven't had any problems with the local law enforcements in either space. I don't want to seem accusatory before a situation happened, the goal is to either see if this practice slides in well with the least amount of in-game friction (new players and Indeps who haven't read are always expected) or now as Rudo points out, work an alternative for a faction who wouldn't have to face both sides of the law in their travels.