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First off, when they attach, do they have to wait until the round after to drain or drain right away?
Second, lets say a guy enters a nest of 30 stirges, how many can attack him at one time? They are tiny and need to enter your square to attack, so there are only so many that fit in a square already occupied by the unfortunate wanderer. In the rules, 4 tiny fit without penalty into a 5 foot square, so possible 8 squeezing. That would seem logical that 4 would fit with a medium also in there.

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It's pretty clear in the Blood Drain(Ex) ability text that the Stirge drains blood at the end of its turn if it's attached. A stirge generally has to:
1) move into a foes space to attack (provoking an AoO)
2) make a touch attack that if successful allows it to attach
3) if attached, it inflicts 1 point of Con damage.
I usually allow up to 8 tiny flying creatures to attack a given creature. Is that RAW, probably not, but generally only 8 creatures can surround and attack another creature.
--Dr. Vrock