In a small city of about 10,000 people- how big should the thieves' guild be?
A rough estimate of organized crime in the US is about 850k in youth gangs. That includes the 3 in 5 who are adults.
Assuming another 150k in other organized crimes is probable... putting the ratio about 1 per 350 or so. BUT...
that's with the current 1.3% farmers. 90% of pre-19th century were farmers... a number stable at least as far back as the Domesday census of England.
So, since most of those gangs are urban, and 5/6 of the US are urban... ... that ups the ratio to about 1 per 300 urban dwellers.
This should vary by culture - the more authoritarian, the more organized crime. Peak rates run to aboput 1 in 50; above that, the parasitic effect is too strong and everyone starves. Minimum rates should be about 1/10, but figures on that are harder to figure.
So, from 1 per 3000 in an absolute democracy with a culture of honesty and fair enforcement of law, to about 1 in 100 for autocratic despotic cultures with no cultural traditions of honesty....
Of course, there's also the D&D solution in 3.X DMG...
1d8+6 for each of two "trees" - with 2x as many at half the level in each.
So a tree with a roll of 1 on the d8 is 1×7th, 2×4th, 4×2nd, 8×1st
A tree with an 8 on it is 1×14th, 2×7th, 4×4th, 8×2nd, 16×1st