Oh man, I feel for you Chris.
With the help of friends, I did the largest section of my roof 2 years ago. There is NOTHING as nerve wracking as hearing thunder and seeing dark skies when your roof looks like this:
It was the first time I had ever done a roof, and I had *really* underestimated the effor needed for tearoff. We got that done the first night, and it was some of the hardest work I have ever done. When I woke up the next morning, I was sore from head to toe... and we STILL had to lay a new roof.
One thing I am really glad we did was to pay an extra few bucks to have a boom truck set the bundles of shingles on the roof. I watched my neighbor run his up a ladder, and it wore him out pretty quick.
I know what you mean about learning who your TRUE friends are!
Anyway, glad you didn't end up with any water damage, that must have been spooky