I started mapping on Source for L4D (and eventually L4D2), then Portal, then dabbled into TF2 until we could modify the Alien Swarm SDK for Portal 2 capabilities. It's funny that, despite using the same engine, designing a map for those three genres of games is completely different. I would have to say Portal is the easiest to design for out of the three, but no less rewarding.
Designing a map for Versus L4D2 and competitive TF2 is when it starts getting serious and difficult.
