TF2 will crash when it connects to a server that has an HTML page when you first login. The solution to solve this back in 6.2 (Mac) was to install IE6 in the same bottle. Please please add this option to the Crossover Games list for compatibilities sake.
Regarding Crossover Games, I'm absolutely amazed. Performance on my 8800GT for mac was incredible! Hopefully Apple will provide better GLSL for dx9, but until then, this is awesome. An instant buy!