I'll apologize up front if this is in the text somewhere and I just haven't found it - I've put in a small effort but admittedly not an exhaustive effort.
How can sprite rogues (without a reach weapon) get flanking?
To flank a foe, you and your ally must be on opposite sides of the creature. A line drawn between the center of your space and the center of your ally's space must pass through opposite sides or opposite corners of the foe's space.
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I believe the answer is "they can't". They could still benefit from Gang Up if they take it, though.
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Does it though? Flanking is usually the most convenient way of getting a flat-footed target, but it's a long, long way from being the only way anyone ends up flat-footed to an attack.
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I ran an encounter recently with Redcaps and Jinkins, and questioned the same thing, until the Redcaps kept succeeding at tripping the PCs, making them flat-footed.
So just add some Jinkins to another encounter.
Sprites as PCs, however, are going to need to be adopted by Kobolds so they can learn to grovel.
That wouldn't have occurred to me, but now I'm curious if I'm missing a written rule. Can a tiny creature end its turn within melee range of another creature, even if its reach is less than 5 feet? Does each creature have to be located in the *center* of its own square?
The quoted text says to use the center of your square to determine whether you're on opposite sides of a creature, but doesn't say you have to use the center of the square to determine if you're in melee range.
Tiny creatures with zero reach have to enter the target creature's square to be in reach. The Sprite ancestry entry specifically references that.
How can sprite rogues (without a reach weapon) get flanking?
Heritage Pixie, the Enlarge spell, Polymorph/Transmutation spell into a small+ creature, ect. If you want to stay small, there is no reason you couldn't get a reach weapon you could use: Ruffian, Bounty Hunter Archetype, Pirate Archetype and Gladiator archetype are pretty straight forward.
Tiny creatures with zero reach have to enter the target creature's square to be in reach. The Sprite ancestry entry specifically references that.
Ah! Thanks. That's what I was missing.
They could still benefit from Gang Up if they take it, though.
That was my stopgap solution. I think it only works one way - the sprite rogue gets flanking and sneak, but the other character will not get flanking. But it's better than nothing, they were going to get Gang Up anyway, and everyone seems happy.
Thanks!
Tumble Behind is another pretty straightforward way for Sprite Rogues to get flat-footed that comes online much earlier; you need to enter the foe's square anyways, may as well derive some advantage from it.