You got a runty little sprite running around between your legs with its 0ft reach stabbing at your ankles. You look down and try to stab them with your sword. Should the GM give it lesser cover against your attack?
Same question but you're a huge dragon with a small goblin climbing up your back.
Cover and Large Creatures indicates that soft cover is from a third creature being between you and your target.
If a creature between you and a target is two or more sizes larger than both you and your target, ...
The basic Cover rules also have the line determining cover being drawn from the center of your space to the center of the target's space. In the case of sharing a space, the only thing that this line would encounter is either yourself or your target - neither of which should be considered as an obstacle. If you have a medium size creature and a gargantuan creature battling each other and not sharing a space, you wouldn't give the gargantuan creature cover because the line between the centers of their spaces crosses through squares occupied by the gargantuan creature.
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I agree that cover is about an obstruction being between the 2 parties involved in an offensive exchange /attack.
However, I do think if a tiny familiar is in the same space as their med master, and something tries to attack the familiar, that familiar gets the lesser cover to pretty much anything.
This is because I don't think there's any rule saying that tiny creatures have a static 1/4 a square, and if they share a square with a med, it means that any line drawn to the tiny creature for a cover check essentially must pass through the med creature.
Note this means that while your example of a tiny sharing space with a hostile doesn't get cover from that one specific creature attacking the tiny, every other hostile swinging at the tiny is hampered by their friend unintentionally granting the tiny some cover.