Help me translate and optimise my 3.5 Monk to 5.0

[Morgarth]

So my group decided to switch the rule set for our adventure from 3.5 to 5.0. I originally played a Human Monk 4 /Swordsage 1/Shadow Sun Ninja 1 so overall my character level is 6.
My DM greatly emphasizes roll playing therefore my character should stay the same. Hence this limits my options to a Human Monk 6 (Way of the Shadow). My problems start at this point, we rolled the stats so my starting array is 16/16/15/15/14/12 . I'm not really sure what I should pick in terms of feats or stats. I already made two builds :

First Build :
Variant Human: +1 Dex +1 Wis Level 4 Stats +1 Dex +1 Wis Feat: Alert
This would bring my total stats to : Str 14, Dex 18, Con 15, Int 12, Wis 18, Cha 15

I picked the Alert feat because it fits the personality of my character and because it should synergies with Diflect Missiles and reduce the impact of being ambushed.
With a +7 to hit, 47 hp and 18 AC I think this could be a good build.

Second Build:
Variant Human: +1 Con +1 Cha Feats: Alert Sentinel (Level 4)
Total Stats: Str 14, Dex 16, Con 16, Int 12, Wis 16, Cha 16

This build is a bit more tanky in terms of HP (53) but has a relatively low AC (16). The idea behind the Sentinel feat is that I could act as a kind of Mageslayer by using using Silence and never let the mage leave the effect by reducing his speed to 0 with the AoO. This said it also encourages the enemy to hit me what might be a problem since I'm not really a tank.


My group consists of five players Paladin, Bard, 2 Wizards and Monk(me :) ) therefore I'm the secondary tank of the group.
My questions over all are:
- Which build is the more potent ?
- Are there even better builds ?
- Are there any points that I'm missing ?
- Could I get better results by multiclassing (and not losing the theme of the character) ?

ps: This is my first Post and English isn't my native tongue so please excuse the mistakes I made (if any)

[Yagyujubei]

I would go the first one. monks get pretty damn survivable to begin with and sentinel is really best served with a reach weapon.

oh and also the fact that you have stunning fist makes it redundant for the most part.

[Chaosvii7]

The good news is that simply by virtue of converting your character from 3.5 to 5e you're already improving your character tenfold, because 5e monks are a huge step up from what the old monk used to be.

I'm gonna vote second build because it's got a lot more tanking potential and anti-magic is a lot more potent in this edition. It's true that Sentinel is best served for reach weapon users but I think it's actually pretty potent with what you're going for.

[Yagyujubei]

but stunning fist achieves the same goal of locking up the caster without wasting the feat (which are a very limited and valuable resource in 5e), and if you really wanted to go anti-mage, then Mage Slayer is indisputably better imho anyway.

[Draken]

On a separate note, you should probably swap your Int and Str around, Str isn't all that useful for you, since you are mostly Dex based, and a good Int score can save you from admittedly rare but rather brutal save or dies.

[Aron Times]

On a separate note, you should probably swap your Int and Str around, Str isn't all that useful for you, since you are mostly Dex based, and a good Int score can save you from admittedly rare but rather brutal save or dies.

Strength saves are more common but they generally come from lesser threats like knocking your character prone or pushing or pulling him on the battlefield. Intelligence saves are rarer but they come with incredibly deadly effects, *cough* Intellect Devourer *cough*.

[silveralen]

Multi classing in 5e is easy to mess up, so I wouldn't. Straight monk will give fairly good results overall as is. Rogue is a pretty safe choice if you do decide to try, but it combos best with abilities like shadow step or cloak of shadows, so it won't hurt to start out as monk 6 anyways.

Feats are tricky. Not a lot goes great with monk. Alert is a solid choice for any situation. Tavern brawler might be worth looking at, it'd bump your con up to 16 and let you make a grapple as a bonus action, instead of the free unarmed attack you get as a bonus action. It might be useful, some people seem to find grappling really amazing in this edition. Mobile is fun for building on the speed of monk, and can work well with way of shadow for a hit and run style of fighting.

If you don't expect the campaign to go into the teens or your DM is okay with retraining feats at high levels, resilient is a good choice. The big thing is that at lvl 14 you gian prof in CON saves regardless.

[Yagyujubei]

as far as MC's go

2 levels into Warlock is a good choice for a WotS monk to get access to Hex and Devils Sight

3 levels into Rogue will get you sneak expertise and assassinate which will greatly enhance your first turn nova if you take the time to set up surprise attacks, and an extra 1d6 from sneak attack doesnthurt either.

for feats I think Mobile synergizes very well with the play style of a monk so that might be something to think about, Grappler or Tavern Brawler do well to facilitate a more wrestler style of monk, in general though I don't think monks get as much bang for their buck by taking feats as many other classes do so getting DEX and WIS to 20 will probably serve you better.

[Morgarth]

Thanks for all the good advice ! :)
I especially like to consider the 2 Level dip in Warlock and think I should look more into grappling/tavern brawler.