With a better militia and the KOTH changes I think TC would go like this.
1. Gang shows up in town.
2. Gang goes to KOTH spot attacks militia guarding it.
3. Gang finishes off militia and takes losses, but if 5 or more are still around start the countdown, otherwise the gang has to wait for re-enforcments to start while militia might start to respawn, making it very hard to take a city.
4. While the countdown is going on gang defends hill from other gangs trying to stop them.
5. Gang finishes timer and takes control.
6. Gang installs militia throughout city(ie respawning captains) and helps defend town while militia builds up. Also I think choosing how militia will behave would be great (ie defend non hostiles/kill enemies of faction/... maybe even attack only members of faction x, y and z.
7. Gang can leave and come back every now and then to collect profits from trading or to defend when another gang trys to attack, safe knowing that it requires a major offensive to take the town.
*Another random thought, it might be possible to make militia charge mine tax (ie if a player doesn't put an ore or mineral in a container before they leave the mine the militia will kill them on the way out.) The ability to choose the laws in a town I think would make them feel a lot more alive.