Snow and lawn service looks like a small line item until the first storm buries the driveway and three siblings each assume someone else already called. Your job is to turn that vague arrangement into a written job with one name on it. Before you ask anyone for a number, decide what you are buying.
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Write the job before you ask for bids
List every surface the crew must clear or cut. For most houses that means the driveway, the front walk, the steps, the path to the side or back door, and any spot a delivery driver or an aide needs to reach. Note the snow depth at which the crew starts, whether they must come back for a second pass, and how soon after the snow stops they should arrive. Name the lawn tasks separately: mowing frequency, edging, leaf pickup, and whether clippings are bagged or left.
Send every company the same list. A bid for the driveway alone and a bid for the driveway, walk, and steps are not comparable, and most mismatched quotes come from this step, not from the companies themselves.
Compare the terms that move the total
Ask each company these questions and write the answers side by side. Are the crew employees or subcontractors, and who answers for damage to the lawn, the mailbox, or the edge of the drive? Ask for a certificate of liability insurance and check that it names the work being done at the property, not only the company. Ask whether a storm that is skipped or only partly cleared is still billed, and whether the plan is per visit, per season, or per storm with a minimum. Ask how pauses and cancellations work, because a winter away or a hospital stay can leave a standing contract running for months.
Decide who holds the gate code and who gets the bill
The agreement should say who holds a key or gate code, who gets notified when service is late, and whose card or account pays. Put each invoice in the family's shared record, not in one sibling's inbox, so the labor and the money show up in the same place.
Make the call
Choose the company that wrote your scope back to you accurately, answered the insurance and cancellation questions in writing, and showed up on time for the first storm without a fight. If the family cannot agree on which company to hire, bring the written bids to the family meeting and let the paper decide. For local starting points, see the local help page.