D&D 5E Choosing between ASI and Feats; how important is a maxed stat?

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First Post
I'm fairly new to D&D, but I've been plotting out different ways I can build my character. It's still early enough that all my options are still open, but the prospect of choosing a Feat at level 4 has me a bit anxious about weakening myself in the long run.

Specifically, I'm multiclassing Rogue(assassin)/Monk(shadow). The feat that I REALLY want is Mobile because it seems essential for hit-and-run tactics, and it would alleviate the problem of having too many things to do on my bonus action (would not have to save Shadowstep/Cunning Action to disengage). I'll also need to play extremely safely because I have 10 Con (I wanted Charisma more). Also it just seems like a fun Feat.

Unfortunately, it seems I'll need to also grab the Alert Feat to make Assassinate work reliably, and at that point, maxing both Wisdom and Dexterity is impossible. After spending some time designing different builds for my ninja, I realized that most have only 4-5 ASI levels, so I'll have to either give up "Mobile" or settle for 16-18 Wisdom. What's frustrating is that the more levels I put into monk, the more I'll want high Wisdom for Stunning Strikes; the more I Stunning Strike, the more I'll want the Mobile Feat; focusing on monk ironically gives me less ASI to work with than if I focused on Rogue levels.

I get that +1 AC and +1 on on Stunning Strikes is important, but as a new player, it's hard for me to quantify mobility and compare it to +2 Wisdom.

TL;DR: is the "Mobile" Feat worth losing 2 points in Wisdom for a Monk(shadow)/Rogue(assassin) build? How do you decide when a feat is worth not maxing an important stat?
 

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TL;DR: is the "Mobile" Feat worth losing 2 points in Wisdom for a Monk(shadow)/Rogue(assassin) build? How do you decide when a feat is worth not maxing an important stat?

Go with the feat, precisely because it allows for you to have more fun and lets you play the character the way you imagine. With low AC's and saves across the board (bounded accuracy) a +1 here or there is not more important than fulfilling your character concept.

Now saying that technically speaking an ability score increase to a primary ability is HUGE. It gives you a +1 to hit and damage, or a +1 to your effect/spell DC's, it most likely increases a good number of the skills your class focuses on, and in the case of Dex/Wis for monk also increases your AC.

For your character a bonus to Wis gives.
+1 DC on stunning strike
+1 AC
+1 on Wis saves (some of the worst saves to fail, and a very common save to make)
+1 on Perception checks and passive perception

Mobile feat give you.
+10 speed, combined with increase speed from monk class makes you the fastest thing in most encounters
Ignore difficult terrain when you take the Dash action, and thanks to cunning action you can Dash as a bonus action awesome
Don't provoke AoO from a creature you attack if you leave his area, allows you to dart all over the map, sure you can do something similar by spending a ki point but this saves you from spending points on that.

I know the math makes +Wis look better, but the feat will probably be more FUN.

I would pass on the Alert feat altogether until Dex and Wis are 20, the +5 to initiative is great but just assassinate the poor creatures who roll lower than you on initiative during the first round of combat.

Oh and welcome to the forums!
 

I would pass on the Alert feat altogether until Dex and Wis are 20, the +5 to initiative is great but just assassinate the poor creatures who roll lower than you on initiative during the first round of combat.

Oh and welcome to the forums!

Thank you very much! You are right, it's probably best to follow my gut and choose fun over optimization. I am hesitant to drop Alert, though. Can an assassin afford to be inconsistent with initiative rolls? I feel like I'd get super frustrated successfully pulling off perfect surprise ambushes and then repeatedly failing to assassinate anyone.
 

You generally only get to attack one opponent at a time, and even without Alert it should be rare for a high Dex character to roll lower initiative than everyone. There'll probably be some poor sucker to crit. Heck, pit fiends or ancient dragons are only rolling +2 initiative at the most. Alert is much more about avoiding being surprised than surprising others.

In any case, Mobile might make sense at level 4, and after that point you'll have a few levels to play around and see if you're really losing a bunch of initiative rolls and want Alert also.
 

You don't need Alert to assassinate. Instead, grab high DX and get a bard to inspire you or something. Consider taking the Lucky feat as well since it's useful both for defense (saves and AC) and boosting your init roll when it's critical to assassinate. Finally, you always have the option of attacking whichever bad guy rolled the worst initiative.

I like Alert, it goes well with certain spells like Fog Cloud/Darkness--but its offensive benefits are quite meh compared to its defensive benefits.
 

I've generally found most players choose the Feat first, then increase an ability, then choose a Feat. What it really comes down to is how important is the Feat to your concept.

As an example, at 4th level as a Rogue/Arcane Trickster who was an archer, I had to decide if I wanted the "archery" Feat (forgot what it's actually called) or increase my Dex to 18. I compared +1 to all attacks, damage and dex checks (of which I did many) to +4 on long range attacks, +2 to +5 against cover, and the option to go with -5 attack for +10 damage. I seldom attacked long range, and the -5 attack was terrible with Sneak Attack, so it really came down to how much I was worried about cover. I decided that cover wasn't that big a deal since I was getting half the bonus already (assuming Half Cover), so I went with the ABI. Glad I did, because I picked up a really cool magic scimitar 2 levels later and switched to melee :)
 

Ive been wondering this myself as well. I have a warlock going for the blade pact, and i was wondering if i should take great weapon master, polearm master, both or just ability increases.
 

My human tempest cleric raised by elves will be 4th level and I'm facing the same dilemma. I love the choices. I took defensive duelist at 1st leve only because it fit my character concept (it has only saved me against 1 hit si far). My cleric only has a 14 wisdom, so I'm stuck - add 2 to wisdom, or go shield master, mobile, or even toughness or healer. Both shield master and mobile fit my character better and they are more interesting than just +2 wis or the other choices.
 


My personal view on ASI vs Feats, is take a feat at 4th level to help you define your character concept and do some other interesting things a feat that gives options not just static bonuses. After that most likely take ASI's over feats until you get to 20 in your primary, then pick up another feat.

But being able to mix and match and it being a difficult choice does mean it is working as intended.

I do wish a few feats were more interesting, not just powerful but more enjoyable to have. Like tough to me I would never take it because it just adds h.p, to me thats boring, but I understand why it is like that same reason the Champion fighter exists, some players don't want to have fiddly options or choices to make they want static number increases and come up with options off the character sheet.
 

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