Well, the title says it...I confronted my fears (on a dare from my kids) and climbed up onto the roof myself! Here's a picture of what I saw when I got up there. You can see how bad the old shingles are.
Everything went fine until I set out to climb back down: I couldn't climb onto the ladder. I pretty much froze, sat down, and waited for Jeff to come hold my hand while I climbed onto the ladder. Once I got onto the ladder, I was okay. Something about facing the drop and having to swing a leg out over it was pretty freaky!