The basic problem is that the stealth rules say, basically: "You can hide when it makes logical sense (according to the DM) that you can hide. Use a Dexterity (Stealth) check to determine how well you're hiding. You can see a hiding creature when it makes logical sense (according to the DM) that you can see a hiding creature. Use a Wisdom (Perception) check or Passive Perception compared to the Dexterity (Stealth) check to determine if someone sees someone who is hiding." Aside from a few rules about vision and lighting, that's it.
That's simple, straightforward, quick to play, super easy to resolve, easy to remember, very intuitive. All good things for rules.
The first crack is Lightfoot Halfling, which says: "Naturally Stealthy. You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you."
Naturally Stealthy contradicts the general rule, because a) it lets you do something you normally can't, and b) it's often not logical. [Crawford insists on several occasions that specific rules can override general rules, but it's hard to tell if a given rule is supposed to override a general rule or merely modify it, so it's hard to be sure exactly what Naturally Stealthy is supposed to override and what it's not.]
For example: a Lightfoot Halfling Rogue can fire a crossbow, move, and as a bonus action hide behind another PC in the same turn. He can do this turn after turn after turn. It's not like you're hiding someplace and nobody knows where you are. Well, unless the monster has the mind of a 1-year-old and cannot grasp object permanence. Mearls has said, IIRC, he'd give repeat hiders disadvantage. That's the primary issue. You can hide even when someone knows which square you're in. Which isn't really hiding, then, is it? I mean, in the context of the game hiding means other creatures don't know where you are. But the rules don't have a built-in consequence for hiding someplace stupidly obvious, which, eventually a barbarian's shadow becomes.
The second crack comes in when you consider that you're not hidden when you're standing behind total cover or when you're heavily obscured -- although you have some similar effects if you're heavily obscured. If you're behind total cover, you just can't be seen as there is no line of sight to you and no line of effect to you, but your location and presence aren't unknown. You could take an action to hide (or a bonus action as a Rogue) but you're not hidden -- creatures remain aware of your presence and you'll automatically be seen when you pop out from cover. That means you won't get advantage for popping out and shooting and jumping back behind total cover... unless you hide. If you hide, then your presence is unknown and remains so until after you attack. There's an understandable dichotomy there because creatures tend to make a lot of noise, but it's still weird.
So, for example, we could have a human Ranger in total cover behind a column who isn't hidden because his location is still known, and a Halfling Rogue hiding behind a Barbarian adjacent to the BBEG in the middle of the room who gets advantage because his location *is* unknown, even though he's spent the last three turns jumping behind the Barbarian to hide again, and basically everybody in the room knows exactly where the little so-and-so is.
Or, how about this. The barbarian is in the middle of a brightly lit 35' circular room with no features. At the north end of the room is one orc. At the east end of the room is another orc. Can a lightfoot halfling hide behind the barbarian? Can he only hide from one orc? From both? From neither? Can one orc tell the other where the halfling is? What if one orc is north and one orce is south?
Or how about just the fact that an archer at an arrow slit and a Rogue at an arrow slit work fundamentally differently because... the Rogue can hide? Again, we're straining credibility. I mean, it's not like the arrow slit moves.
I know how I would rule in all the above cases, but it's not even a little clear what the designers think should happen here. That's the problem. It's hard to tell what designer intent is.
If you want a third crack in the stealth/hiding/vision/lighting system, you can consider the poorly phrased wording of heavily obscured: "A creature in a heavily obscured area effectively suffers from the blinded condition." So, a human standing 100 feet from the entrance to a cave which opens to broad daylight cannot see any creature standing outside the cave because he's blind. And our Ranger above moves into an unlit adjacent room suddenly can't fire his bow into the adjacent room because he's now blind. That makes total sense, right? That one is thankfully easy to ignore because I think most reasonable people know what it's trying to say. But, you add in less realistic stuff like darkvision, blindsight, and truesight which modify how obscurement and light works in general, and there's a lot that is either unclear or makes no sense.
A fourth crack -- although it's not much of one -- is trying to decide when you should use Perception and Passive Perception. Again, it's a DM's call and that works well enough, but it's not clear when the designers think you should switch between the two.
So the errata comes out and says: "Hiding (p. 177). The DM decides when circumstances are appropriate for hiding. Also, the question isn’t whether a creature can see you when you’re hiding. The question is whether it can see you clearly."
This clarification is roughly as clear as the text it's attempting to clarify, because the first sentence can contradict the second and third. See, it doesn't really say much of anything. It slightly informs what the criteria are for trying to hide, but since "clearly see" is an unclear term in most senses, it's still pretty ambiguous.