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Conditions can only be applied once during a round. But the AC penalty for entangled or grappled would stack because they don't give the flat-footed condition.
Pinned is a different story. It does give the flat-footed condition so a character can't be "double" flat-footed. The character would take -2 AC from flat-footed, then an additional -4 to AC for the Pinned condition.
Edit: Yea, what Metaphysician said!

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No matter how many things say you are flat-footed, you only take the flat-footed penalties once. Penalties from any other conditions also apply.
Since pinned includes flat-footed, you take -2 AC and can't take reactions. Since pined says "You also take an additional -4 penalty to your AC, attack rolls, Reflex saving throws, initiative checks, and Dexterity-based skill and ability checks" you know that you are at a total of -6 to AC, and -4 to the other things.
If something else then makes you flat-footed again, there's no change.
But if you get sickened, it's penalties all apply, stacking with those for being already pinned and flat-footed.