Hide in Plain Sight is a weird, WEIRD ability. HIPS lets you use Stealth in situations where you otherwise couldn't. Unfortunately, not all HIPSes are created equal, and there are a bunch of different versions floating around. These are the ones I could find with a quick AON search:
RANGER CLASS FEATURES
Camouflage (Ex): A ranger of 12th level or higher can use the Stealth skill to hide in any of his favored terrains, even if the terrain doesn't grant cover or concealment.
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Hide in Plain Sight (Ex): While in any of his favorite terrains, a ranger of 17th level or higher can use the Stealth skill even while being observed.
ROGUE ADVANCED TALENT (10th level minimum)
Hide in Plain Sight (Ex): A rogue with this talent can select a single terrain from the ranger’s favored terrain list. She is a master at hiding in that terrain, and while within that terrain, she can use the Stealth skill to hide, even while being observed. A rogue may take this advanced talent more than once, each time selecting a different terrain from the favored terrain list.
VIGILANTE TALENT
Hide in Plain Sight (Ex): The vigilante can use Stealth to hide even when being observed. As long as he is within 10 feet of dim light (his own shadow doesn’t count), he can hide without anything to actually hide behind. Only a stalker vigilante of at least 8th level can select this talent.
FORESTER HUNTER ARCHETYPE
Camouflage (Ex): At 7th level, a forester can use the Stealth skill to hide in any of her favored terrains, even if the terrain doesn’t grant cover or concealment.
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Hide in Plain Sight (Ex): At 14th level, while in any of her favored terrains, a forester can use the Stealth skill even while being observed.
ASSASSIN PRESTIGE CLASS
Hide in Plain Sight (Su): At 8th level, an assassin can use the Stealth skill even while being observed. As long as he is within 10 feet of an area of dim light, an assassin can hide himself from view in the open without having anything to actually hide behind. He cannot, however, hide in his own shadow.
SHADOWDANCER PRESTIGE CLASS
Hide in Plain Sight (Su): A shadowdancer can use the Stealth skill even while being observed. As long as she is within 10 feet of an area of dim light, a shadowdancer can hide herself from view in the open without anything to actually hide behind. She cannot, however, hide in her own shadow.
SHADOW ORACLE REVELATION
Stealth Mastery (Ex): You gain Skill Focus with the Stealth skill. At 8th level, you gain Signature Skill with the Stealth skill, even if you don’t meet the feat’s prerequisites. At 16th level, you gain the hide in plain sight shadowdancer class feature.
CLOAK OF STONE FEAT
Prerequisites: Wis 17, Stone Cover, Stone Shroud, Stealth 11 ranks, dwarf, stonecunning racial trait.
Benefit: You can use the Stealth skill to hide even while being observed while you are in areas of rocky terrain or while underground. You can hide yourself from view in the open without anything to actually hide behind as long as you are within 10 feet of rocky terrain, or at any time while you are underground.
CIPHER INVESTIGATOR ARCHETYPE
Hide in Plain Sight (Su): At 7th level, a cipher can use the Stealth skill to hide even while being observed; as long as his observer is within range of his inattention blindness ability (even if it is not affected by inattention blindness), he can hide without anything to actually hide behind.
COMMANDO GUNSLINGER ARCHETYPE
Camouflage (Ex): At 11th level, as long as the commando has 1 point of grit, she gains the camouflage ranger class feature.
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Hide in Plain Sight (Ex): At 15th level, as long as the commando has 1 point of grit, she gains the hide in plain sight ranger class feature.
CULT LEADER WARPRIEST ARCHETYPE
Hide in Plain Sight (Su): At 12th level, a cult leader can use the Stealth skill even while being observed. As long as he is within 10 feet of an area of dim light, a cult leader can hide himself from view in the open without anything to actually hide behind. He cannot, however, hide in his own shadow.
SABOTEUR ALCHEMIST DISCOVERY
Greater Chameleon Mutagen: The saboteur’s chameleon mutagen now also grants the saboteur the hide in plain sight ability, as the ranger ability of the same name, but it functions in any terrain. The saboteur must be at least 12th level to select this discovery.
SHADOW CALLER SPIRITUALIST ARCHETYPE
Umbral Aura (Su, Sp): At 10th level, a shadow caller is wreathed in an aura of darkness while her shade inhabits her shadow, gaining 50% concealment against creatures without darkvision or the see in darkness ability. Additionally, the shadow caller’s square and all adjacent squares are treated as areas of dim illumination while she benefits from this ability; this second effect counts as a 4th-level darkness spell for the purpose of adjudicating light and darkness effects. While her shade inhabits her shadow, the shadow caller can hide in plain sight, even if an observing creature has darkvision or see in darkness.
Broadly speaking, HIPS tends to come in two flavors: ranger-style, and shadowdancer-style. Ranger HIPS usually requires you to be in a Favored Terrain, while shadowdancer HIPS usually requires you to be within 10 ft of an area of dim light. FT is, like so many other ranger things, extremely feast or famine--you're either in your FT or you're not--so without a bit of finagling, it can be cumbersome to manage. The terrain bond spell lets you treat your current terrain as your MOST favored FT, which is nice for the higher bonuses, but it's SL4 and therefore somewhat annoying if you're in and out of different environments frequently. I prefer to just have a bunch of boots of friendly terrain, since they're cheap and stack with your real FT bonuses.
Shadowdancer HIPS's dim light proximity requirement is a different kind of fussy. Your own shadow isn't enough, but that specific carve-out implies that someone else's shadow might be. Or, like, environmental shadows. If so, how big of a shadow do you need? And how does low-light vision affect it, given that LLV, from the perspective of the person who has it, extends the "normal light" band of any existing light source twice as far? Light levels are not absolute or global, so whose POV are we using to decide whether or not there's any dim light nearby? The sneaker? The enemy they're trying to sneak past? An unaided human standing where the sneaker currently is? If LLV makes that torch bring the whole room up to normal light from Eric the Elf shadowdancer's perspective, but not from Hannah the Human shadowdancer's, is Eric just screwed, or can he, like, use Hannah's shadow as a fallback? In short: WHAT?
There are two conditions that must be met in order to start sneaking/use Stealth: you must have either cover or concealment, and you must not be observed. Shadowdancer HIPS waives both at once; ranger HIPS only waives the observation requirement, requiring other abilities to waive the cover/concealment requirement (usually, Camouflage, which ranger-likes get earlier).
Cover/concealment is pretty easy to parse. Both are relative, so you just check if a prospective sneaker has cover or concealment from the viewpoint of the enemy. Shelving unit between them? Cover. Foggy morning? Concealment.
But observation is … awful. What it means to be observed is pretty fuzzy. Ultimate Intrigue's rules for stealth and detection HELP, but they don't entirely fix the problem. And in a game without facing, even concepts like precise vs imprecise senses and undetected/hidden/concealed/observed can get wibbly.
Ultimate Intrigue pg. 188 says "The reason a character usually needs cover or concealment to use Stealth is tied to the fact that characters can't use Stealth while being observed," implying that breaking line of sight (or other precise sense) via cover or concealment is itself enough to satisfy the observation condition. It goes on to say "The hide in plain sight class ability allows a creature to use Stealth while being observed and thus avoids this whole situation," and this is, strictly speaking, TRUE, and for the purposes of shadowdancer-style HIPS that's enough because it deals with both observation and cover/concealment … but ranger-style HIPS is split in half across two separate abilities. And this is grandfathered in from at least D&D 3.5 so clearly it's on purpose and it's supposed to DO something.
What, then, is the point of Camouflage? It only waives the cover/concealment condition, not the observation condition. So a ranger with Camouflage but not HIPS does not need cover/concealment to hide, but they DO need to not be observed, but cover/concealment are necessary precisely BECAUSE they impede observation, so … again, WHAT? Under what circumstances would Camo be helpful without HIPS? Say there's a Camo ranger in their favored terrain with clear line of sight to a sentry--does Camo let them skulk around so long as the sentry hasn't noticed them at all yet (i.e., the sentry is "unaware"), only to collapse entirely if the sentry ever does realize they're around (i.e., the sentry is "aware of presence" and that instantly upgrades past "aware of location" straight to "observing")? If so, when does the ranger roll that first Stealth check? Does Camo let them hang out in the open at the end of a Stealth-movement instead of needing to dart from obstruction to obstruction?
(Nota bene: I briefly thought that this confusion might be a casualty of the Hide/Move Silently skill consolidation during the 3.5 -> PF1 transition, but nope; the Camouflage and HIPS abilities for 3.5's ranger both specify Hide.)
… In conclusion I really want to know what RAI is, here, because right now I have no goddamn clue.
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