**Spoilerism**
Do not read this post unless you are a DM, or the mighty gods of something or other will smite you, verily!
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I too had an infiltrator, and it All worked out pretty well.
My advice would be to cover your bases - make sure you have several logical scenarios under which the switch can be made. My party decided to turn themselves over the the authorities after the "assault" on the inkeeper, sidestepping the scenario I had in mind. I opted then for an interrogation session in which the relevant party member was swapped.
In addition, make sure that EVERY character is alone at some point or another, and make sure to bring up this point at the relevant time if the party doesn't bring it up.
I also invented a magical pair of amulets which allowed the doppelganger to access all the knowledge and abilities of the duplicated creature. It made things much easier, as the replaced PC's player could still make use of feats, class abilites, etc. This may also remove the ability of the party to detect the doppel early, but I found it easier to do things this way (the doppel player was less experienced than the rest of the players)
In addition, I had these amulets work both ways - the PC was privvy to the thoughts and unguarded knowlege of the doppelganger. This way, when the real character was rescued, she was able to pass on info about the doppelganger gang in a more natural way than me just telling them what's happening. Fianlly, they were destroyed when one of the two parties was killed.
To cover why the doppelganger would willingly attack and kill its compatriots, I had overwhelming thoughts of cold-blooded ambition about Ixaxian working its way up the gang's heirarchy via attrition. I had vague visions of a tentacled monster strike cold fear into the otherwise fearless and arrogant doppelganger's mind, hinting at the true mastermind of the gang.
My final piece of advice: Try to END a session with the party entering the room with their duplicates. You'll probably get a lot of valuable info in the post-game chit chat, as they talk about their discovey, their theories about who might be an imposter, and how to determine who is who. You and your stooge can also work out some exact battle plans. I managed to do this, and it worked well - the players had all that time between sessions to stew on it, theorize, and draw wild conclusions, and I had time to come up with why the druid's animal companion did not detect any scent differences (magic amulets to the rescue!).
Good luck - I think the switch is definately worth it!
The idea with the amulets is brilliant, and I'm totally stealing it.
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Sorry for the thread necromancy but I had to tell someone: Last session. I pulled it off with an infiltrator.
At some point before Elaxan, everyone has had some alone time so that anybody could be the doppelganger.
The party slew Elaxan and now knew that doppelgangers were about. One of the player's aunt (a noblewoman in Wavewatcher's Bay [using Christopher West's Lands of Mystery map from Dungeon #150]) warns the players, "Anyone can be a doppelganger. Trust no one; not even the DM." I felt that a little fourth wall break was important for reasons which will become apparent.
So the party gets to the Hall of Reflections and everyone sees their double. The players are my wife, our eight-year old son, a married couple, and an engaged couple. At this point, I pause to explain the situation to our son. We've tried to instill in him the importance of honesty. And I wanted him to understand that one of the players was just pretending and not really lying; that it was part of the game. He listened attentively and seemed to take it seriously. The rest of the group began to try to ferret out the doppelganger.
Between the players they could all recall that everyone had been alone at one point so it really could've been anybody. They finally made their selection and they chose . . . poorly.
Because it was my son all along (not even my wife knew). He pulled it off swimmingly! They never suspected him. The engaged guy was bent because he felt I had tricked him as opposed to the villains. I reminded him that he'd been warned not to trust the DM. The married guy doesn't enjoy that sort of shenanigans, but admitted that it was well done. His wife loved it, thought it was amazing and that the guys were being petty.
We have the next session in a few hours. The doppelgangers get sneak attacks in the surprise round. And they'll change into different players every round giving them a kind of blur effect except that instead of a 20% miss chance, it's a 20% chance to hit the real person instead of the doppelganger. But it's the Week of Feebleness where everyone does minimum damage, so it should be okay.