The oak by the garage hangs over the roof, and the maple by the back fence has a limb that moves in every wind. You want them looked at. Then the first bid comes in and you cannot tell why it is what it is. A tree price is a handful of decisions stacked on top of each other, and most of them are visible from the yard if you know where to look.
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The things that raise the bill
Height and reach matter most. A crew working from a bucket truck on a clear driveway can do in an hour what takes a crew most of a day with ropes, because the rigging takes time. Access matters just as much. A crew that can park at the curb and carry debris a short way is in a different job from a crew that has to haul limbs through a narrow side yard or over a fence.
Disposal changes the total. Ask whether the price includes hauling away the brush and logs, grinding the stump, and leaving the yard raked. If it does not, the bid is a starting point, not the finished cost. Limbs over the roof or near the power lines raise the risk, and risk gets priced in.
Timing plays a role too. A crew with a full schedule charges what the schedule allows. Ask whether the work can be done when they have an open slot, since that is often the only lever you have. Work that has to happen right after a storm often costs more than planned work, because it arrives all at once.
The things that lower it
Doing the work in the slower part of the year, clearing the access path yourself before the crew arrives, and cutting the list down to the trees that really need work all help. Some towns require a permit to remove certain trees, which adds time and sometimes cost. Ask whether the crew handles the permit or whether the household has to.
Compare two bids on the same list
Walk the yard with a notebook and write down each tree, what you want done to it, and what is over the house, the fence, or the lines. Give the same list to every company. Then compare the bids line by line: what gets cut, what gets hauled, what gets ground, who pulls the permit, and whether cleanup is included. A cheaper bid that leaves the brush on the lawn is not actually cheaper.
Ask every company for proof of insurance, and check that it is current and covers liability and workers' compensation. An uninsured crew working on your property is a risk you should not carry for the sake of a lower number.
What to do tonight
Stand in the yard with him and point at each tree. Ask him which ones Mom liked and which ones worried her. Take photographs from the street and from the back fence. Don't climb anything, and don't let him climb either.
When to call someone right away
If a limb is touching a power line, do not go near it. Call the utility's emergency number and stay back. If a limb has come down on the roof or a window is broken, cover the opening from the ground with a tarp if you can do it safely, and call a company with an emergency line. If a tree is leaning toward the house, get an arborist out before the next storm, not after it.
A good-week note
A good week is one where you have three bids on the same list, each one spelled out line by line, and you both know which trees come first.