My MacBook Pro doesn't like monitors.

This is post #2 on the matter. My last question that I posted on this topic looks to have been deleted.
I'm having an issue, well, a few issues, with my Late 2008 MBP 2.53Ghz, 4GB Ram, 320GB HD. Its a stock configuration with the only thing having been upgraded is the OS.
It crashes. A lot. But they're not kernel panics, its something to do with the window manager when I plug in and unplug USB devices and/or a display. There's nothing in the logs that indicate that something has crashed.
Just this morning I put my iPod in its dock while it was playing without headphones, took my computer out of its bag, connected the power, the USB hub, they USB Keyboard, then the display and before I could wake it up the iPhone was stuttering, wouldn't respond and then restarted. The computer was completely unresponsive. The monitor didn't even respond that it had been connected to something.
Most times I'll have problems with unplugging my display. I can unmount and unplug the USB devices (Apple keyboard, logitech mouse, iPhone dock & external Seagate hard drive) but unplugging the display will cause the system to hang and the fans to spin up.
Its not a hard crash, though. The window manager, or something, is becoming unresponsive. I can SSH in from another computer and kill just about every process running but can't get the computer to become responsive again.
I've reinstalled the OS a few times now and keep having the same issue.
Can anyone help?

Hi Shawn, I have the identical machine. I have not had the issues you speak of. I plug into a 24" LED cinema display daily along with similar USB devices. I noticed you mentioned you are using 10.5.5, perhaps try to update to 1.5.6; Also, try to update the firmware in your display adapter (if not using a display with the mini display port). I know there were some firmware updates for the display adapters (http://support.apple.com/downloads/MiniDisplayPort_to_VGA_FirmwareUpdate)

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