OK, this is curious. I was just trying this again, a few times, and it's not actually the moment you step into the portal that it crashes, it's the moment you're entirely out. Even if your vision is on the other side of the portal, if any of your collision box is still in the portal, the game seems to keep running. I'll need to try this again.
Huh. That's not exactly it either. I went most of the way through the portal, and stood there for about five seconds, looking around, everything apparently fine, then it crashed.
I stood without going through the portal, throwing the radio and clipboard and cup peices through it. After about the same amount of time, it crashed.
Yeah. This time I didn't interact with the portal in any way, and it still crashed after about the same amount of time.
So if you run into the portal, it crashes right away. If you do nothing, it crashes after several seconds.
...
WHAT THE HELL
I coppied over some save files from another computer, and loaded them up. It worked. I created a portal. It worked.
I'm uploading a video now. (The video is only a few FPS, terribly low quality, I was recording it only so I could accurately keep track of when the game crashed, not for the content itself.) This is confusing as hell. There's something about the first level that causes the game to crash, but it's not the portals.
The video should be here when it's finished.
Bah. This makes my head hurt.
EDIT: The first level doesn't crash in the commentary mode.
I've played through the first 15ish levels with no issues, until it decided to crash. I think this was unrelated to the other stuff though, so me happy.
EDIT: No, it's crashing whenever I start playing, either a saved game or a new game, a few moments after the level loads. Aaaaaaarg.