If someone has an example map with some flags in it I'm sure I could use that to figure it out. Source instructions do not work. I'm using J.A.C.K. at the moment because I couldn't get the regular hammer editor to work with the modern steam infrastructure, but I've been able to successfully compile and launch a map so I'm sticking with it. Just haven't been able to get the flags to work.

In Day of Defeat 1.3, once a team captures all the flags the victory music plays and everyone goes back to spawn and a new round begins. That's essentially all I'm after.