For some of the lower stuff possibly. It's a good idea if only to protect the glass. However, I'd say it's worth it to remove some of that street side fence and speed line everything out to the chipper at the curb. It migtht not be necessary to remove the fence but it's really hard to tell by the picture. Then use a block and portawrap to rig the stem down.
Always hard to tell from the picture. Usually end up with major sudden expansion of the tree when you see it in person
I think it more likely they will send someone out and tell you you have to remove every tree within striking distance of the house at your own expense or else they'll drop you like a stone.
