First, the silly question:

What do I do to get new textures to work?
I downloaded a bunch and they've got both the .vmt and .vtf extensions but .. where do they go?

Also, is there a way (admin mod maybe) that can determine the winner of a map and alter the mapcycle.txt?
My idea is a sort of daily "campaign" starting with Omaha and the following maps are, more or less, a road to Berlin. Though a little pointless considering the number of maps right now, eventually something like this might be really neat.

Thanks in advance.

Found the directory ...

About your second question, I am coding a new admin tool at the moment aimed at DOD:Source and yes this would be possible since you can evalute who win and alter the next map. But I really don't see how this would be since you said it youself, map that have real city name are not legion.

We do run a campaign right now in 907th that is based a bit on the RISK game. I coded a application that keep the scoreboard, match result, territory owned, challenging sytem.

In 907th we have six company and they all fight to conquear Europe.

You can look at the rules, map and scoreboard at :

http://www.907th.com/risk/scoreboard.php

Everything is automated except for the map itself since we need to change the color of a country manualy. Not what you have in mind but I thought it might spark some interest and give you idea. still it's very far from your idea.

To come back to your initial idea, it would probably be hard to find someone who would code that for you if you can't code yourself.