This achievement normally takes a LONG, LONG time. But with this session, depending on how many players sign up, we COULD get it in as little as 20 minutes of work!
Here's how this will work. You get credit for winning this map as long as you are on the winning team. My server is configured so that teams do not have to be balanced (so 12 people can be on the same team with no one on the other team). Additionally, there is no idle timer, so you will never be kicked.
What we will be doing is meeting up and agreeing to take shifts. We will agree on "shift times" and each of us will take one shift for a certain amount of time (depending on how many people show up) and just grind out wins, for which everyone gets credit. At the end of your shift, the next person steps in, you go do whatever you want to do, and reap the benefit of someone else playing.
By using scout, and immediately capping, you can win this map in about 1 minute, 40 seconds. This comes out to a little under 4 hours of total play time needed to get all 138 wins.
If this works out well, I will do the other "win X number of games on map X" in subsequent weeks.
Boosting Gaming Session for Team Fortress 2