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Message: <blockquote data-quote="MostlyHarmless42" data-source="post: 7482767" data-attributes="member: 6845520">While I'm on the fence about Magic Initiate, I do like the idea of a magical familar. That said, were I rolling this character I'd probably take Mending, Mage Hand, Prestidigitation, or Vicious Mockery as cantrip options over what you listed. The first would be amazing for fixing/moving objects on a ship (i.e. rope), prestidigitation has a number of fun uses (who doesn't want a color changing hat?), and Vicious Mockery fits the idea of a swashbuckling pirate all too well. Another serious feat option to consider? Crossbow Expert for "pistol" wielding fun. Also, I'd consider Athletics as an expertise, or possibly Vehicles (Water) if the DM will allow it, as the former involves climbing and grappling (tavern brawls?), and the latter would make you a Great captain instead of a "meh" one. After all, if you are going high dex and have proficiency you'll already be passable at stealth, and if the dice do go south, you're the party face: you WANT to be noticed!Again I think you undervalue athletics as a skill. A sniper would probably take full advantage of climbing in order to find good perches. Also, Cha and Charlatan is sort of up for personal preference. I could also see you going Wis or Int with acolyte and go for a more religious vibe. You could pick a god of death or whorship the concept of a "perfect kill" or something. Alternatively if you want full infiltrator you could go spy and be a James Bond-esque assassin. Again I suggest crossbow expert rather than sharpshooter if you are planning the infiltrator route as you'd likely find yourself in close quarters in an infiltration scenario and a good hand crossbow works well. For sniping moments switch to a heavy crossbow and go nuts. You could still take sharpshooter if going full sniper.</blockquote>

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