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

[Slit518]

I have a character who is a Variant Human Assassin, and I want to know what you think are the best feats for it?

I am a Strength based Rogue, with Expertise in Athletics.

I have a Charlatan background, which gives me a believable False Identity.

Stats are:
Str - 17
Dex - 10
Con - 12
Int - 9
Wis - 14
Cha - 14

Skills are as follows -
Athletics *
Deception *
Intimidation
Investigation
Persuasion
Sleight of Hand
Disguise Kit
Forgery Kit
Poisoner's Kit
Thieves' Tools

Languages -
Common
Elven
Draconic (to speak to lizardfolk)
Dwarven
Giant
Thieves' Cant

Linguist feat

 

[Mort]

The assassin rogue benefits massively from going first in a fight.

Since your Dex is low, Alert is near mandatory for this build.

 

[Gladius Legis]

Alert, Alert, and Alert.

Yeah, it's that important for the Assassin.

Any particular reason for STR over DEX?

 

[Slit518]

Alert, Alert, and Alert.

Yeah, it's that important for the Assassin.

Any particular reason for STR over DEX?

The character himself is 5'9", and weighs 255lbs. He is a short, stocky fellow, who is a mix of fat and muscle. He has a lot of strength packed into his size, think of a bulldozer.

He is an assassin that depends on his alternate identities to get close to targets and assassinate them.

I combo grapple with attacking, if only an assassin could get an extra attack.

The Expertise combined with Athletics makes grappling most normal enemies a breeze.

I was thinking of taking a level of Barbarian to gain Rage which gives me Advantage on my Athletics checks, aka, Advantage with Expertise on Athletics.

I need 20 Strength.

Also, in certain grapple situations I can can Advantage on my attack rolls, triggering Sneak Attack damage.

A Rapier can either be used with Strength or Dexterity, making it ideal for a Rogue whether Strength or Dexterity based.

 

[Ath-kethin]

Magic Inititate (Wizard): mage hand, prestidigitation, sleep. It's the best feat for basically every character that isn't a wizard, and you could make a case for wizards taking it too.

Prestidigitation provides distractions, mage hand is, well, mage hand, and sleep is a literal knockout. Can't be beat.

For your concept, maybe disguise self or silent image instead of sleep. But still.

 

[Slit518]

Magic Inititate (Wizard): mage hand, prestidigitation, sleep. It's the best feat for basically every character that isn't a wizard, and you could make a case for wizards taking it too.

Prestidigitation provides distractions, mage hand is, well, mage hand, and sleep is a literal knockout. Can't be beat.

For your concept, maybe disguise self or silent image instead of sleep. But still.

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.

 

[CTurbo]

Alert all the way, but I'd be worried about your terrible. Moderately Armored may be your best friend. It will round out your Str score too.

1-3 of Warlock would be great to get some face invocations like Mask of Many Faces. Hex could get you medium armor and expanded crit range too. Chain gets you a beefy familiar.

 

[UngeheuerLich]

Ok... your AC is terrible. Your intiative too. Your stealth also. Only his false identity helps and that is a very late ability of the assassin class.
So i would really recommend two feats:
- Actor which is really good helping you to assume roles
- maybe tavern brawler to allow attacking and grappling at the same time.

I'd also actually recommend to think about different classes than rogue.
As mentioned warlock and mask of many faces is really useful. Maybe if you should come into a fight armor of shadows could prove useful. I really don't think that hex is useful here. I'd rather go for fey patron to either frighten or charm a target and access for the sleep spell. And armor of agathys if you are attacked.
A different Idea is going bard and rogue or even bard only with college of whispers. You also get access to expertise and on top you get charm person, sleep and disguise self spells. Rounded out by the friends cantrip which has no drawback if you kill your targrt anyway as well as the enhance ability spell for advantage on strength checks or charisma whichever you need more. Then there is an invisibility spell to get where you need.

One thing to remind you to: if you want to multiclass with rogue, 13 dex is mandatory. Since you don't really get any benefit from 9 int and 17 str (except for when you take the tavern brawler feat), you can lower them to 8 and 16 respectively and also have 13 dexterity without any drawback.

A last idea which might not the worst one would be drop bard and rogue alltogether. Take the human feat from xanathar's guide: prodigy which gives you a skill, a tool, a language and expertise in skill (athletics) and then go full out barbarian/fighter.

TLDR:
rogue with 10 dex can't multiclass
A different class than rogue might be more to your liking

 

[Slit518]

I get an alternate identity as a background feature.

It comes with the paperwork and connections which make it seem real.

 

[UngeheuerLich]

I get an alternate identity as a background feature.

It comes with the paperwork and connections which make it seem real.

Yes. So assiassin is even less needed.