I've tried popping it in and out and didn't have any luck. I've also tried watching for the screen blink and disconnect sound. I don't know if it helps, but I can access adb shell in command prompt via USB debugging. I don't know if that matters, but at least that should mean it's no longer a driver problem right?
YAY! It finally worked.
maybe today was just the perfect storm.
PNY SD Card
10 Min Root Video (Minus HTC Sync) - simple after you get the right error
RootWiki Usb Driver
PRS Rooting Guide (Method 3 is what it took)
Thanks to everyone for their help. Especially Doug!