You are an expert at slinking through shadows. You gain the following benefits:
You can try to hide when you are lightly obscured from the creature from which you are hiding.
When you are hidden from a creature and miss it with a ranged weapon attack, making the attack doesn't reveal your position.
Dim light doesn't impose disadvantage on your Wisdom (Perception) checks relying on sight.
Skulker: Hide and Sneak
Review by Sam West, Twitter:@CrierKobold
Ah, hiding rules. A nebulous, wildly varying system table to table that can range from World of Warcraft’s “crouch = invisible” to an overly aware band of enemies that can smell the dust you kick up when you only get a 19 to hide forty feet away behind a whole house. Skulker, more so than any of the rules baked into the game, highlights how hiding actually works, which on its own adds value to its existence. Skulker teaches us that you need to be at least heavily obscured to hide normally, attacking reveals your position, and dim light imposes disadvantage on perception checks (normally used to determine if something senses a hidden threat).
Removing these three penalties for your character can be one of the greatest boons a rogue can receive; it also can be entirely worthless with next to no meaningful upsides. It all comes down to the value of hiding in your games and how your DM specifically runs and interacts with hidden creatures. For how I personally run games, despite my best efforts, I think Skulker would end up feeling pretty useless largely because I offer ample places for characters to hide, and rogues routinely can refind cover after moving to hide at. Plus, I basically always forget to incorporate dim light rules at the table, because I just can’t juggle one more extra layer of rules to running perception in my games.
While how I specifically run games isn’t going to match your experience at your table, I would hazard a guess to say Skulker likely isn’t going to offer you that much value, even in the best cases. You need to be finding a good chunk of lightly obscured areas to justify it, as it opens up a new avenue of play to you. The other effects are neat, and better on characters who can’t use a bonus action to hide, but rogues can’t really get that much benefit from not being revealed, as they’d normally just spend their bonus action rehiding anyway. This puts it in a weird catch-22; rogues don’t have much need for the second line of text, but nearly every other character in the game can’t afford to be actively hiding in combat to get the most out of the feat. The lightly obscured hiding matters a lot less if it's something you’re not interacting with round to round, but just once before a fight. It makes it so non-rogue characters can’t really get as much as they’d like from the feat, either. Plus, when you consider you could simply bump your Dexterity score up by 2 for a +1 to all Dex rolls, I can’t imagine this is worth it.
Still, if you are a rogue finding yourself exclusively surrounded by light foliage, or can use two or more allies to qualify as giving you an area that is lightly obscured, I can see this being something you’d look to pick up. At tables where hiding is genuinely hard, and there aren’t many spaces to do it, opening up more can be a game changer for specific rogue builds. Outside of that, the text here doesn’t really justify taking it. You’re probably better off with just a +1 dex mod.
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