Eh. The Assassin henchidiots Leeroy no more than the Warrior henchidiots - they just have shadow steps to do it faster. :P But since half the missions and primary quests seem to involve Mhenlo or Master Togo Leeroying on you, I'd definitely say that Factions is the one to get last, despite the access to Alliance Battles (12 vs 12 PvP) which gives you Balthazar Faction very quickly.
As for which is better for getting skills for PvP, I think Nightfall is generally considered to have the most powerful skills overall (the exception being [[Dragon Slash] for Warriors, which is in Factions), especially for Elementalists.
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