How does the racial feature Mask of the Wild apply in practice (how is it beneficial?)

Question

My interpretation of Mask of the Wild is that players with this feature are able to hide in situations that other players are unable to. For example, a wood elf can attempt a stealth roll in heavy rain, while other players would not be able to because it is too easy for them to be seen without this feature. This has been my interpretation based on a fair bit of reading and sticks to RAW more than offering advantage etc.

Unfortunately I am struggling to find ways to apply this feature in most circumstances. The feature only helps in situations associated with natural phenomena, so towns, dungeons, vessels, palaces, etc. are largely excluded from the feature. But when I consider a forest, I recognize that all players can attempt to roll stealth checks by hiding behind trees easily enough. It seems silly to imagine a situation in which only a wood elf can hide but others cannot (you're in a forest, but all of the trees are so skinny that only a person with Mask of the Wild can hide?).

It seems Mask of the Wild is only helpful when natural phenomena are not enough for the average player to hide, but are still enough for a wood elf to hide (moderately tall grass, short bushes, very light forest, heavy rain or snow in open spaces, and moderate but not heavy mist outside of forests), which seems relatively limited. In addition, I would probably need to make effort as a DM to create these types of situations specifically to allow mark of the wild to be beneficial. I don't typically differentiate between forest and light forest, or tall grass and taller grass.

I am running a campaign in the jungles of Chult, which presumably almost always offers an opportunity for any player to attempt to hide, which makes things worse.

How does Mask of the Wild apply its benefits in practice? When is this a beneficial feature?

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This question is different from the other question How does the Wood Elf's Mask of the Wild trait work, in terms of flavor? as it relates to the mechanical benefits of the feature, rather than flavour.

Answer 1

Wood Elf whispers to Goliath "Go hide somewhere else"

Yes, you have the right of it.

It is on the DM how powerful Mask of the Wild is. You can make it useless by hand waving that all forests are heavily obscured, or not obscured at all. Or you might make all forests light obscurement, making it very useful.

It is all about how obscurement affects a character's ability to use stealth. Normally, once you have been seen, unless you are in or can get to a heavily obscured area you can not re-hide. Wild elves can hide even if someone is watching them with only light obscurement.*

HIDING

The DM decides when circumstances are appropriate for hiding. When you try to hide, make a Dexterity (Stealth) check. Until you are discovered or you stop hiding, that check's total is contested by the Wisdom (Perception) check of any creature that actively searches for signs of your presence.

From the Stealth section of the PHB

What is lightly or heavily obscured?

A given area might be lightly or heavily obscured. In a lightly obscured area, such as dim light, patchy fog, or moderate foliage, creatures have disadvantage on Wisdom (Perception) checks that rely on sight.

A heavily obscured area--such as darkness, opaque fog, or dense foliage--blocks vision entirely. A creature effectively suffers from the blinded condition when trying to see something in that area.

The DM is there to make a call on what kind of obscurement the environment offers. It is not necessarily given that any character will be able to hide behind trees. I always think of a pine forest. Tall skinny trees with very little branches below 30 ft or so. A moderately dense forest like this would probably only be lightly obscured, or even mot obscured. So while the rest of the party be seen after they attack, the wild elf can use the sparse ground cover to "disappear" back into the treeline.

The good news is that it doesn't have to be a decision made ahead of time. When you get asked about how heavily obscured the environment is, make a roll. Vary the probabilities based on the environment.

eg. This jungle is lightly obscured one time out of 20, otherwise it is heavily obscured. This changes every 100 yards. OR Springtime rains in this region normally roll in in the early afternoon, and last for 1d4 hours. Most of the time there is a heavy downpour, ,making the area lightly obscured (1-15); sometimes it really opens up making everything heavily obscured (16-19). On a roll of a 20 the rain has eased up to a light drizzle. This changed every 30 mins.

If you decide to make it random beforehand; and tell the players, then you have consistency and fairness, more realism, with less work. And you have it right there to refer to anytime you get asked. After all, even the densest of jungles have clearings, and the lightests of fogs may have thick patches.

*This has all kinds of rule caveats and DM decisions surrounding it. I really recommend reading all of the following PHB sections for more on obscurement and stealth:

Vision and Light

Stealth - especially the hiding sidebar

Also this podcast gives some nice DM tips on running stealth.