What are the best feats to pick for my Human Assassin build?

Slit518 said:

That is tempting, though I should of mentioned (I forgot), that he is a bit weary, and I would go as far to say, hates magic.

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Well, that changes things a bit.

If you want a cookie cutter, there have been many fine suggestions, and you can't go wrong with Alert for your concept, or really any concept. A little more outside the box: Linguist helps with disguises and infiltration, especially if you aren't using magic. If your character HATES magic, consider Mage Slayer.

Healer is always useful. Keen Mind is great for spying.

If you're playing D&D like a combat board game, many of these ideas will be less useful. If your game is more immersive and out-of-combat focused, they can really add dimension to your character.

My recommendations: Two in total, one left and one right.

The Charleton Background makes one of Assassin's main features, Infiltration Expert and Imposter, redundant. Yes, with the Assassin features, you can make more false identities, and with the level 13 ability you can make it so you don't need a check while the Actor Feat merely gives you advantage, but if you have Charleton and actor, you can make any class into the Assassin.

The only difference is Assassinate and Death Strike, for massive damage. But Assassinate will be used very rarely. And Death Strike, if you ever get there, is amazing, but again, the creature has to be surprised, and the DC is keyed off your Dex modifier, which in this case is extremely low.

So, with your build, you will likely not get to use Assassinate, as you are not stealthy, and will not be going first due to low initiative. You seem to like the "pretend to be someone else, sneak up and kill someone", so if you went Charleton and Actor, you can do that pretty easy. If you took a magic class with access to Disguise Self, like Warlock, you could do this all day long, having the Charleton False Identity as one of the faces you can conjure. With Actor, you can pretend to be anyone and look like them too. I've done that combo. Went through the entire Redguard base in Lost Mines of Phandelvor with a Warlock with Mask of Many Faces, pretending to be Glasstaff, led my party all the way to Glasstaff, killed Glasstaff and scorched his body, then told "my" men that someone had snuck into "My" office, and we've been found out so we all have to leave town. Defeated the entire dungeon with only one kill. Then I took Glasstaff's staff and started calling myself Glasstaff. Cause my last name is Glass.

If you don't want warlock, or hate magic, then just go Fighter with the Actor Feat and Charleton background. That gives you all kinds of nifty fighting toys to play with, and you won't be beholden to a rapier. Just shove an ax down their throat. You won't get massive damage to one attack per round, but you'll get multiple attacks and lots of options. Go with Champion for the increased Crit threshold, and crit 10% of the time for your massive damage.

The strength based rogie is an archetype missing. The champion or battlemaster are good replacements though.

[MENTION=6803713]Slit518[/MENTION] Cool concept, clearly you're thinking character first and it shows with a unique and interesting build that will still be plenty effective. To get the most out of your assassinate ability, I'd go Alert at 4th, then work to up your strength with Tavern Brawler (giving you a +1 str as well as a bonus action grapple) at 8th and then +2 Str at 10th. Past that you could pick from Actor, Lucky, Mobile, Medium Armored, Tough, or Keen Mind depending on how your character evolves during play.

Take level 1 Fighter then Rogue levels. Fixes your armor. You can use duelist so your damage doesn't drop to badly.

I'd go Battle Master Fighter, wear Breastplate with the Defense Style. Take Charlatan, Actor, Diplomat, and Silver-Tongued feats. Take 1 level of Great Old One Warlock for telepathy, and Mask of Many Faces. = Profit

Maybe even take Inspiring Leader at some point in the future. You could end up as sort of a Warlord character using the Commander's Strike and Rally maneuvers.

By the way, the character is level 3, and is 3 sessions deep.

I chose Assassin for the Assassinate feature. Initiative is only important if there is combat, assassinating somebody might be something to do to avoid combat.

For example, a captain of the guard is walking around, talking, I'm disguised as my alternate self. He thinks everything is fine and safe with his old pal around, then BAM! Rapier to the guts!

Slit518 said:

By the way, the character is level 3, and is 3 sessions deep.

I chose Assassin for the Assassinate feature. Initiative is only important if there is combat, assassinating somebody might be something to do to avoid combat.

For example, a captain of the guard is walking around, talking, I'm disguised as my alternate self. He thinks everything is fine and safe with his old pal around, then BAM! Rapier to the guts!

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I don't understand how you can live 3 levels using a primarily melee character with 11 ac.

Slit518 said:

I chose Assassin for the Assassinate feature. Initiative is only important if there is combat, assassinating somebody might be something to do to avoid combat.

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You still need to beat your target's initiative to Assassinate. Which is why we're all questioning just how effective this build is going to be.