I really
like the Men-type encounters in the AD&D Monster Manual. The listings
include all kinds of rolls to flesh out the group of ne’er-do-wells, be that
Bandits, Brigands (which are, we learn, chaotic evil Bandits), Buccaneers,
Pirates (that is, chaotic evil Buccaneers…) or what have you.
Generating
them on the fly is a pain in the ass, but during prep/hex stocking you can
create the whole group that has a lair and sends out patrols/raiding parties in
their area.
Here’s a Bandit group, rolled up by hand:
THE BLACK SNAKES GANG
Leader: 10th level fighter
Lieutenant:
7th level fighter
Personal
guards: 6 x 2nd level fighters
Elite
fighters: 3 x 3rd level fighters, 2 x 4th level fighters,
1 x 5th level fighter, 1 x 6th level fighter
No magic-users
or clerics.
Regular
bandits: 60
Equipment (total no. of combatants: 75):
medium horse, chainmail & shield, sword 10% 7
light horse, leather armor & shield, spear 10% 7
light horse, leather armor, light crossbow 10% 8
leather armor & shield, sword 40% 30
leather armor, pole arm 10% 7
leather armor, light crossbow 10% 7
leather armor, short bow 10% 8
Lair:
Type:
informal camp
Important
prisoners: 12
Camp
followers/slaves: 15
Treasure: 4,000 sp, 4,000 ep, 300 pp, 40 gems
So this is what you get just from the Monster Manual.
For additional details, I would use my humanoid lair generator. The Black Snakes lair in a ruined manor, they are plagued by inner strife and low morale. Perhaps all those elite fighters are planning a coup.