How many tiny creatures can occupy the same square as a medium character.
I will use the example of Stirges. If there were 15 stirges, how many would be able to enter the square of the unfortunate medium character?
Being tiny creatures, four can occupy a five-foot square (Core Rulebook p. 194).
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That's total in a 5' square. What about them attacking and occupying the same square as a medium creature. That part referenced does not mention it.
Tiny, Diminutive, and Fine Creatures: Very small creatures take up less than 1 square of space. This means that more than one such creature can fit into a single square. A Tiny creature typically occupies a space only 2-1/2 feet across, so four can fit into a single square. 25 Diminutive creatures or 100 Fine creatures can fit into a single square. Creatures that take up less than 1 square of space typically have a natural reach of 0 feet, meaning they can't reach into adjacent squares. They must enter an opponent's square to attack in melee. This provokes an attack of opportunity from the opponent. You can attack into your own square if you need to, so you can attack such creatures normally. Since they have no natural reach, they do not threaten the squares around them. You can move past them without provoking attacks of opportunity. They also can't flank an enemy.
That's total in a 5' square. What about them attacking and occupying the same square as a medium creature. That part referenced does not mention it.
I would still answer four. It says they must enter the opponents square to attack. How many can fit into a square? Answer: four.
I will admit I remember in 3.5 seeing a FAQ or Rules article that said something like half the normal number can attack, but I can't find a reference to that and that would still be unofficial.