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This is something I have been wondering for a bit. I am currently playing with a Rogue/Warlock Mousefolk build. Here is the link to the Mousekin homebrew race I am playing. I am planning on a build of 12 Rogue/8 Warlock.

As my character is quite small, I wanted to go a stealth/speed route, so I wanted to get the Skulker Feat with the One with Shadows eldritch invocation. To be hidden from enemies would be the main goal of this build, as the campaign I am currently in has a number of encounters. (However, advantage on attack is a second for the bosses.)

So can I hide in dim light/darkness, use OwS, ranged weapon, hide, and then use OwS again? Also, how many actions would it take for me to pull is off? Is this build worth the trouble?

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    \$\begingroup\$ Welcome to the site! Please take the tour when you get the chance. It's important to remember that there are thousands of RPGs out there; can you tell us which game and edition you're asking about? \$\endgroup\$
    – Oblivious Sage
    Commented Feb 22, 2019 at 20:45
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    \$\begingroup\$ Could you clarify what you wanted to get out of this tactic? For example, wanting "to have advantage on attacks" or "to have your enemy not know where you are" would be very different goals, and would alter whether we might consider this build "worth the trouble." And finally, could you possibly specify how many levels you were planning on taking in each class? \$\endgroup\$ Commented Feb 22, 2019 at 21:14
  • \$\begingroup\$ It has been edited. @BlakeSteel , it is the One with Shadows Invocation. \$\endgroup\$
    – a Cit
    Commented Feb 23, 2019 at 4:31

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There may be no need for One with Shadows.

To analyze this, we should look at what Hiding (the action) does versus Invisibility.

In the Hiding sidebar (PHB 177), it says

An invisible creature can't be seen, so it can always try to hide.

In addition, the condition Invisible (PHB 291, emphasis mine) says

An invisible creature is impossible to see without the aid of magic or a special sense. For the purpose of hiding, the creature is heavily obscured. [...]

Attack rolls against the creature have disadvantage, and the creature's attack rolls have advantage.

There's a lot of crossover here. The main benefit of Invisibility for this build over "hidden" is that you 1) can always hide, and 2) you always get advantage on attack rolls, which will always trigger sneak attack.

Unfortunately, for this build, One with Shadows ignores point 2, since it's not continuous, so it only gains "you can always hide". This is fully negated by the Skulker Feat, because it allows you to hide in even dim light, and you can't turn invisible with One with Shadows unless you're in dim light. One with Shadows has its uses, but usually not in a rogue, since they can use their bonus action to hide. The only real benefit for this build is that you can hide from enemies with darkvision in dim light, whereas you normally wouldn't be able to, but I don't think it's worth your action in combat, and you should try to find darkness or cover instead.

Action economy with One with Shadows:

Turn 1. Move to dim light or darkness, use One with Shadows, bonus action Hide.

Turn 2. Attack, bonus action Hide, move again

Turn 3. Move to dim light or darkness, use One with Shadows, bonus action Hide.

Repeat steps 2 and 3.

Action economy without:

Turn 1. Attack, move to dim light or darkness, bonus action Hide.

Turn 2. Attack, move again, bonus action Hide.

Turn 3. Attack, move again, bonus action Hide.

Repeat steps 2 and 3.

In the first version, you're guaranteed advantage and sneak attack, but you attack half as much. In the second, you attack twice as much, and will likely get sneak attack, as a creature must actively Search for you to contest your Hide.

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    \$\begingroup\$ The text of One with Shadows says "When you are in an area of dim light or darkness, you can use your action to become invisible until you move or take an action or reaction. \$\endgroup\$ Commented Feb 22, 2019 at 21:55
  • \$\begingroup\$ Oops. I misses that. Nvm \$\endgroup\$ Commented Feb 22, 2019 at 22:04
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    \$\begingroup\$ I think you are very slightly short-selling One With Shadows. If you become invisible, it doesn't matter whether the opponent has darkvision. But if you only have Skulker, then dim light won't lightly obscure you from an opponent with darvision. \$\endgroup\$
    – Ruse
    Commented Feb 23, 2019 at 1:44
  • \$\begingroup\$ Ok, but what about the benefits of Skulker? From you are saying, you can use Skulker to hide, OR OwS to turn invisible. So you cannot be invisible and hide at the same time? \$\endgroup\$
    – a Cit
    Commented Feb 23, 2019 at 2:03
  • \$\begingroup\$ Because you only have 1 action a turn, that's a very poor strategy. Turning invisible is an action with OwS, and Hide is a bonus action as a rogue. Because there's very little benefit to having both active at the same time, and there's not much that OwS that isn't offered by Skulker and Rogue combined, it's most likely not worth taking, and certainly doesn't optimize damage. \$\endgroup\$ Commented Feb 23, 2019 at 6:28

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