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Message: <blockquote data-quote="Esker" data-source="post: 7640035" data-attributes="member: 6966824">If you are on board with having your damage spread out over multiple attacks, then you want Fighter 5 for action surge and extra attack, probably going battlemaster so you can layer on some additional dice (even with advantage, you'll likely need precision attack not infrequently if using sharpshooter, and you may want something like menacing attack in case you don't manage to finish the job in your first turn, so the creature can't approach you; maybe trip attack to use on your last attack if you have melee allies who will be able to go between you and the target). Alert is essential for an assassin, since you have to beat the target in initiative. And crossbow expert coupled with extra attack and action surge gives you six shots on that key first turn. So I'd probably aim for Fighter 6 / Assassin 4 at level 10. Then three levels of Ranger for Gloomstalker goodies (additional initiative bonus, plus yet another attack with extra damage in the first round), and a nice feature to help you surprise creatures relying on darkvision. And at that point, another level of ranger gives you another ASI. So at level 14 you're up to five feats/ASIs if variant human: alert, crossbow expert, sharpshooter, +4 DEX. Or you could take the ranger levels earlier, delaying crossbow expert and using hunter's mark as a substitute until you get it.</blockquote>