http://bugs.winehq.org/show_bug.cgi?id=26835
--- Comment #38 from ntan1 arch_slayer@yahoo.com 2011-04-19 14:25:37 CDT --- It seems like the biggest issue for getting portal 2 to truly be playable (with workarounds) is the communication component between client.dll and server.dll.
It seems that Portal 2 queries some Steam server (or maybe your instance of Steam) to do verification of your game instance, and a failure in said verification is causing the crash. I suspect GameOverlayRenderer is somewhat related, and there have been issues with client-steam server communication in the past (check other games that force authentication with Steam).