SOURCE: Player’s Handbook

Skulker’s Stealth Boons

Skulker has three benefits, and they’re all circumstantial:

Benefit #1 – 

You can try to hide when you are lightly obscured from the creature from which you are hiding.

Stealth normally requires heavy obscurement, so depending on how your DM runs stealth and light and heavy obscurement, this can be a mild benefit or a great one.

Benefit #2 – 

When you are hidden from a creature and miss it with a ranged weapon attack, making the attack doesn’t reveal your position.

This feature is rarely useful; remember you have advantage on your attacks while hidden from a creature. How often do you miss when you have advantage? This often gives you another chance to land an almost certain hit, but if the DM rolls initiative right then and there, they may try to find you with a perception check or throw an AoE effect in the general direction of where the attack came from.

Benefit #3 – 

Dim light doesn’t impose disadvantage on your Wisdom (Perception) checks relying on sight.

Many DMs handwave dim light imposing disadvantage on perception checks, especially on characters with darkvision, but this is useful for avoiding ambushes, seeing things in an all-darkvision party, etc. Remember that as Jeremy Crawford once said, the third benefit of the Skulker feat is beneficial to you whether or not you have darkvision because darkvision gives no benefit in dim light and turns darkness into dim light for you.

Mechanics and Requirements

Understanding How It Functions

The stealth rules are patchy, spread across multiple sections of the Player’s Handbook, and are run differently from table to table. How stealth works in practice is that you ask your DM if you can hide, and if they reckon you can hide, you roll stealth against in most cases, the enemy’s passive perception, though some DMs just have the enemy roll perception.

The first bullet point of Skulker is a problem with this loose interpretation of stealth: lots of DMs will let you hide in some bushes, but if it’s at all possible to see you if someone’s paying attention, that’s technically light obscurement. It’s entirely possible you won’t get any benefit at all from the first bullet point of Skulker.

The second bullet point is straightforward enough. The third bullet point, however, is something else that alongside the first bullet point, benefits greatly from a DM who’s a stickler for running things like stealth and perception. Even if you have darkvision, dim light is still disadvantage on perception checks, so having a lack of disadvantage is super helpful.

Key Stats

Unless you’re aided by certain magic, need a good dexterity and stealth proficiency (or even expertise) to make use of this feat.

Ideal Characters for Skulker

Top Classes

Rogue – Rogues are sent out to do sneaking a lot. Whether or not sending a lightly armored single non-disposable character out is a good idea depends on the situation, but rogues often have expertise in stealth, so if only light obscurement is available, and the target of their scouting is in dim light, this is the perfect feat.

Ranger – Rangers have a special spell they acquire at level 5 called Pass Without Trace; this abomination of a spell gives a +10 bonus to stealth checks, possibly to the entire party.

Druid – Same with the ranger, except they get Pass Without Trace at level 3. Honorable mention goes to the Way of Shadow monk who can run away with incredible speed if caught, but druids tend to be more effective party members than monks overall.

Multiclassing Considerations

Three levels of druid, Way of Shadow monk, or Trickery Domain cleric, or five levels of ranger, are enough to get you Pass Without Trace. Three levels of Warlock can allow you to recover Pass Without Trace uses on a short rest if you have some feature that gives you the spell and lets you cast it with your slots, such as…

Race or Subrace Choices

The (Monsters of the Multiverse) Earth Genasi is the ultimate pick for a stealth character due to their ability to cast Pass Without Trace for free once and with their spell slots as often as they like.

The Wood Elf is the worst choice to pair with Skulker despite being seemingly thematic since the Wood Elf can already hide in light obscurement from natural phenomena.

Combos, Tactics, and Synergies

Complementary Feats

Skill Expert (Stealth) is a great pick; might as well make sure your stealth checks in light obscurement actually succeed.

If for some reason you are a Wood Elf, Wood Elf Magic isn’t the worst pick

Spells that Synergize

Pass Without Trace is the best spell for boosting stealth rolls, but remember that the rest of your party can’t hide in light obscurement unless they have a feature that allows them to. Invisibility can allow you to bring your friends along; you hide in the bushes, they walk around in the open, and you all have a +10 bonus.

When To Take Skulker

Ask your DM how they run stealth: if you can just hide in bushes or behind anything at all and they don’t care about dim light giving disadvantage on perception, skip this feat. But if they’re a stickler for perception rules and whether or not something is light or heavy obscurement, this may be an okay, but not great, pick.

Is Skulker Any Good?

Skulker isn’t that great of a feat. Shadow Touched turns you invisible if you really want to hide perfectly, but if you’re a character who’s not meant to be a magic user and you don’t have any other good feats, perhaps if you’re a rogue, and your DM runs things in a way that makes Skulker useful, you can make Skulker into an okay pick.

…But raise your primary ability score first. That’s more useful.