Sir Brennen
Legend
Why should doing it more than once become harder due to conditions that already prevail in the first attempt, and for which Naturally Stealthy doesn't factor?
Because as soon you make that first attack, that in itself changes conditions.
But a sidebar first...
It's hard to separate out the Naturally Stealthy ability into another equivalent example, because NS seems to give you the ability to hide - become unseen - under circumstances where you'd normally be seen, specifically, partial cover from another creature. Add to that the assumption that the halfling can see his opponent while thus hidden, that means he can attack while still hidden, thus granting advantage. His location is revealed once he does, so he has to hide again to get the same advantage. This seems to be the popular interpretation of the ability.
A less ambiguous example of pretty much the same ability for Wood Elves is Mask of the Wild. Normally you can see someone that has Light Obscurement, so they can't hide from you. But Wood Elves can (for certain types of Light Obscurement). They can hide - become unseen - but can still see you to attack under circumstances where you would normally be able to see them right back.
If it's a human rogue hiding behind a wall, well, to hide they have to be unseen, meaning total cover, and if they have total cover, they can't see the enemy. To attack they have to put themselves in a position to see you, and therefore, to be seen. So no advantage for attacking unseen. As I've stated before, if you were hiding before the enemy was aware of your presence, I'd allow the first attack with advantage, but after that, the enemy is paying closer attention to that spot.
So, as I said, the attack changes the circumstances - you've made the enemy aware of you, and your immediate intention to do them harm, and your tactic of sniping from your current location. The enemy paying specific attention to this and not, as others have said, acting like a Keystone Cop, falls under the "use common sense" statement in Mearls' answer. For the human rogue behind the wall, it negates his ability to attack unseen (for that target). For the halfling, it just makes it harder to keep hiding behind the same guy.
Obviously, over the course of this thread, there has been disagreement over the human rogue scenario I described. Some say a successful Hide still allows you to peek around the cover and make an attack unseen. Going with that logic, the scenario is then very similar to the Naturally Stealthy ability... Hide, attack with Adv, location revealed, need to Hide again, repeat. If you keep doing it from the same spot, the target is going to get wise sooner rather than later.
Now, if the first Hide attempt is during combat when your location is already known, which would be the same conditions as later attempts? Why was the first one normal and subsequent ones at disadvantage? Well, for Naturally Stealthy, a DM might rule the first was at DisAd too... "I totally see you moving behind that fighter and trying to hide!"* However, I think a ruling more in the spirit of how the ability is meant to be used would be the first attempt is normal. The enemy reasonably expects to still be able to see you somewhat behind half cover, not to completely disappear from view.
But once you attack... if you don't kill the target, they're going to think "Oh! You were there the whole time! I know to watch out for that now. Fool me once..."* The target's knowledge of what's going on is the condition that has changed, hence the subsequent disadvantage.
What Ilbranteloth and I have been saying, is that one way to counter this knowledge, is to do something different, even if that's just moving to a new spot to hide.
*Translated from Orcish
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