[R@S]

Entering hostile cities
There are several ways to do this, you can wear enemy uniforms and they wont turn hostile directly and that gives you a few seconds to clear the immediate area. Or you could rush for cover, it's what I usually does. Try entering through the spawn point nearest to the hospital, that buildings gives you many options. You can go inside, up on the roof or use the corners to wait out the enemy, the aim-at-point function will save you in those situations.

If you want to use dark as cover, the time between 00 and 03 is the most effective.

Militia will be "grown" if your funding is big enough, but it takes time. How fast depends on reputation and how much funding your militia has. I dunno how many militia men you can have in a city, I've had 200 when I set the funding to max and waited a few weeks. There is however a limit to how many militias there can be in a loaded city, which is 35, all else is regarded as patrols that will attack the city if an enemy patrol captures your city.

The AI doesn't pick up weapons the player drops, but it does pick up weapons fallen comrades drop and I think also their enemies' weapons.