When homeowners send us a competing quote and ask why ours is different, the answer is almost never the cutting. Dropping a tree is the fast part. The money is in what happens to several tons of wood afterward, and that is the line most quotes leave vague.
Ask whether haul-away is included or whether the wood stays. "Debris left on site" is a real and legitimate option — some people want the firewood — but it needs to be a choice you made, not a surprise you discover on Friday afternoon. A mature oak can leave two truckloads of logs in your yard, and the company you call to remove them second will charge more than it would have cost to include it.
Ask whether the stump is in the price. Removal and grinding are separate operations with separate equipment, and plenty of quotes cover only the first. If grinding is included, ask to what depth, and what happens to the grindings.
Ask what "cleanup" covers. Raking and blowing the drop zone is different from a sweep of the whole yard, and after a storm the debris is rarely confined to where the tree landed. Small twigs across a lawn are a real afternoon of work for somebody.
Ask for the insurance certificate, not a verbal yes. If an uninsured cutter is hurt in your yard, or drops a limb through your neighbor's roof, that becomes your homeowner's policy's problem. Any legitimate company will send the certificate without being pushed.
Finally, ask what happens if the scope changes. Trees hide things — a hollow trunk, a hornet nest, a second tree leaning on the first. The honest answer is that we stop and re-price before continuing, in writing, so the number you approved stays the number you approved.