Tree Service, ask for insurance before job?

[Martin S.]

Have a huge oak tree which has roots pressing against the foundation. Want to cut it down before it causes any real problems. I did have it trimmed, and they dropped large logs onto the roof, which put a small 2 inch hole into the roof and caused a leak 8 months later once enough twigs and leaves caused the roof to allow water to pool when it rained. I had to book a flight, car rental and hotel to get down there myself and take care of the leak and a couple other issues. It was probably cheaper than hiring a roofing company, for some reason every time I try to outsource some work, no matter how small they give me insane estimates (Sarasota, FL). To install 2 security lights an electrician wanted $600, obviously cutting down a tree costs an insane amount of money, redoing the duct work for the central hvac is like $4.5k, flooring, installing a door or window or anything is just ridiculous.

Anyways, I requested a few quotes. Some came back over $5k, but I did get one at $3k, which I am considering, since it is a very large tree and they will take everything away...

Should I ask for a copy of their insurance policy before the job starts? I don't want to end up on the roof again fixing holes or shingles sticking up with debris under them...