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I had the same issue with redsnow "waiting for reboot" on my xp machine. (I originally jailbroke my 3g on the XP machine when 3.0 first came out with no issue). I tried it 4 or 5 times including the "unplug and plug back in" tip but to no avail.
I ended up trying it on my vista pc and it worked...
I jailbroke my 3G right after the 3.0 update. I had always wanted to but I too was afraid it would screw up my phone.
I guess the reason I chose to after 3.0 was released was because I was pretty pissed that with the 3.0 update Apple didn't give the 3G the video recording option or the battery...