Bawylie
A very OK person
I'll try to answer this example.
The primary problem here is that we don't have enough information. This is set up as a traditional "Checking for random traps" kind of trap, which just inherently doesn't work well with goal & approach. Is there any reason the players would suspect a trap here? Why? What clue or signal were they given that this door is dangerous?
So let's just assume that, for whatever reason, they have been led to believe that there's a trap here that can be discovered if they just look really closely. (As an aside, I would hope they got that information in an interesting way, or they had to figure out that the hint applied to this door, otherwise the resolution is just as mechanical & uninteresting as just "rolling for traps" in every 5' square.) If that's the case, and a trained rogue looks really closely, shouldn't he succeed? Why do you still want to roll to see if he succeeds or fails? To me, that's like making somebody roll Athletics for climbing a ladder. (EDIT: Actually, that's like having some interesting roleplaying/puzzle-solving in order to find the secret ladder going up the cliff, and then requiring them to make the same Athletics check to climb the ladder that they would have had to make to just climb the cliff.)
Now let's look at another variant: the heroes have gotten a clue that there's a magical trap here involving writing, and if they [insert some task to accomplish] they can disarm it. They haven't yet accomplished the task, but the rogue is impatient and wants to see if he can disarm it without going through all that trouble. So he says, "I'll examine the door carefully using a magnifying glass, but if I see any writing I'll stop before I read the whole thing." Now, I have no idea if this approach would work "in real life" (for obvious reasons) so this isn't a matter of player expertise trumping character expertise. But as the DM I might think, "Hey, that sounds pretty cool. I'll accept that as a valid, if risky, approach." So I say to the rogue, "Let's roll some dice to see if it works, but if you fail...or maybe if you fail by more than 5...it's going to trigger the trap. As the expert rogue you know that's a risk, so you can back out now if you want."
How about if I offer a real life example, which I used just last night. My players had recently acquired an old house, which they had been led to believe contained some clue that would further their mission. In their inspection of the basement I had included a description of a wine storage room, filled with those diamond-shaped bins that each hold multiple bottles of wine, and also one shelf designed to cradle 10 bottles, slightly angled so the labels would be on display, as if meant to hold the "good stuff".
In going through the piles of ledgers and paperwork and receipts trying to learn who lived here and why it was abandoned, one of the (many) clues they came across was a sort of bar-code like diagram: 10 skinny rectangles in a row, some filled in neatly, some empty. At this point I was actually nervous they would make the connection too soon, but hey that's part of the game.
Ok, meanwhile they had gotten to know some of the neighbors, including a mysterious lady with her household that included a spooky little girl who had a penchant for cryptic prophecy. When they rescued the lady, as part of the thank-you scene the little girl said, "Have you found yet what you're looking for under your house?"
The players go running back to the house, and start searching all kinds of stuff. Not a single die rolled, though. Somebody specifically mentions the chimneys (and in fact specifically the chimney in the kitchen on the first floor, although I wouldn't have required that) so I described how the flue seemed like a strange design. They poked around in it, and I revealed that it looks like the flue joins another flue coming up from below.
They pull out their floorplans for the house, look where the fireplace is in relation to the basement, and realize that if there's a secret room below, it must be on one particular side of the basement, so they go down to carefully search all the walls facing in that direction. Which just happens to include the wall of the wine room that contains the display rack. This time when I describe that shelf, with its 10 spots, one of the players sits up and says, "I get that case of wine we received as a gift and put bottles in the (he looks at his notes) first, third, sixth, and seventh positions."
Click.
The table cheered, big smiles on their faces. Not a single die rolled. No out-of-game expertise needed (although there would have been some required to figure out what 1010011000 is when converted from binary to decimal, which nobody thought to use, despite having that expertise. Which is fine because it was an easter egg, not a necessary part of the plot.)
Now maybe you don't agree, but we thought this was way more fun...and WAY more rewarding/gratifying...than taking turns rolling Perception ("Can I roll, too?") in every 5' square until somebody "succeeded" by randomly getting a high enough number on a d20. I know because I asked them, specifically with this thread on my mind. And I didn't even phrase the question that derisively.
Gosh-darn awesome example. Love it.