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Back to the painting - - you as the DM might have hidden a clue in the painting - like he appears to be holding an unusual looking key which looks familiar. You might set the DC of finding the clue at perception DC 20. The above mentioned paladin will on seing the picture - (passive perception 21) hey that's interesting that key looks familiar. In the case of no one having passive perception high enough - one of the players has to be bright enough to think - why did the DM put a painting here - I'll make a perception check to check it out - needing to get 20 to notice the clue - if the roll(s) fails or noone makes a perception check (and no one has high enough passive) clue is not found. Not all clues need to be found. Of course with critical clues a hint from the Dm is an idea if the players have "lost it". Players can learn and become more competant and interesting roleplayers (two separate developments) - - -etc


Passives are great equivalent to an active check with a die roll of 10. e.g. Many times in our game the high passive perception characters are not surprised by the ambush and the low ones are   

It sounds like you want to 'lead' your players a little too much.

For instance, in the painting scenario, personally I would just describe the scene. 'You walk down the corridor. On the wall to your right is a painting depicting a man doing some stuff'. I've given the players information and clearly stated something of interest in the corridor. It is up to them if they choose to stop and look at it. If they do say 'I want to take a closer look at the painting' I would then say 'you notice the man in the painting is the villan you are chasing'. As previously stated, if there was a 'hidden clue' in the painting, that would have a DC attached to it, but I would NOT allow passive perception to be used to detect it. The PCs would have to make an active check to have a chance of finding it, otherwise they will just miss it. THeir choice.

The reason for this, is because of the word 'passive'. The way I work it is this.

If the players don't know something is happening (they don't know they are being lied to, or they don't know something is trying to stealth around them) then I make rolls vs their passive skills. This is because the players are NOT being active at the time (they can't because I have given them no cue's as to what is going on). If, however, they ARE being active, so they are saying 'I want to search this chest', then only the active check matters. Even if they have a passive perception of 21, if they roll a 15, the check is 15 and that is what I use their search result. Again, this is because they are being active, and that roll represents how well they performed that particular action.

EXAMPLES

Passive Perception

Players are walking through a forest. They are being stalked by a pack of Wolves that are waiting for a good time to strike. The wolves roll stealth (either one for each wolf or one for the pack, depending on how you want to run it). If any player has higher passive perception than the stealth rolls, I will say to that player 'You notice some movement out of the corner of your eye over to the west'. It is then up to them to take action. They may decide to ignroe it and carry on, in which case I will repeat the process until such time that the wolves attack (with suprise). If they decide to take action, I will let them do what they want. Maybe explore, maybe set traps, maybe make active perception checks. Their active perception checks will be rolled against the previous stealth checks, and if they succeed, they will fully notice one/many wolves.

Passive Insight

Two NPC's in a bar are talking and one is trying to rip the other off and the players happen to overhear the converstaion. The NPC doing the ripping off will roll a bluff check and any player with higher passive insight will be told that they believe the NPC is up to no good. It is then up to the players to take action.

Important Note: When reporting the results of failed checks, BE AMBIGIOUS. If they fail an active insight, don't say 'You don't notice anything special' as players will know that this means 'we failed the check so there might be something up'. Simply tell them 'You believe the man is telling the truth'. This way, they don't know if they succeeded or failed in the check, the only know that they believe he is on the level. Giving players as little meta information as possible will keep them 'in the game' and in character.

Active Perception

A room has a secret door in it. As the players enter the room, they decide to have a close look around. If they roll high enough, they find the door. Simple.

Active Insight

A salesman comes up to the players and says he can sell them a magic elixer that will make them all twice as strong for 1000gp. The NPC, who is obviously a con man, will roll a bluff check. The players to take action. Either walk away, or do an active insight check, or buy the potion. If they do active insight, it will be vs the bluff check. If they succeed, I will say that there is clearly something off about the man and his offer. If they fail, I will tell them they believe he is telling the truth.

General Rule

Use passive skills when players have no cues to go on, and use the passive skills to lead players into making decisions and taking action. Use active skills when players are clearly attentive and activley attempting to achieve something.