Food for thought:
1) A mighty warlord, like a Dr. Pain, should be able to TAKE what he wants
2) In raping and pillaging, they should also have the option of destroying
I've always thought it humorous that someone like Dr. Pain was rampaging
through the country side, killing everything that breathed, and yet, he'd
have to stop and haggle with the local merchant regarding the price of
longswords :) It's fun to think about, but it would make warlording too
attractive in a lawless society like Olympia.
However, leaving mayhem in his wake is the right of every mass murderer.
The city/town/market destruction could be temporary (a couple of months)
just until the local populace recovered from their 'doctor's visit'.