So the other day I was at a commercial building where my 32' ladder was just a tad too short to get to the eave. The guys suggested that I just put my big ladder on the roof of the detached garage, and lean it onto the building that way. I politely declined, although I'm sure it would have worked fine. There is a limit to how I'm willing to risk myself. How I actually got onto the roof probably wasn't much safer, but at least it didn't involve me trying to hoist a 65lb ladder up onto a roof. That would have been a nightmare and taken three guys to help me. I took a picture.
https://lh3.googleusercontent.com/p6...=w1698-h955-no
I had a 40' ladder today for a claim, but we ended up not needing it for that roof. However, since it was what I had with me, I had to use it on my next claim which definitely didn't need it. That ladder is so tall that it reached the gutter on a two story house without even being extended.

