Tree removal spans a wide range of difficulty and risk — it's worth being honest about which end of that range your specific tree falls on before deciding.
A small tree — generally under about 20-25 feet, with a clear, open drop zone well away from structures, fences, vehicles, and power lines — is within reach for someone genuinely experienced with a chainsaw and basic felling technique: reading the tree's natural lean, cutting a proper directional notch and back cut, and having an escape path planned before the first cut. If any of that is unfamiliar, this still isn't the tree to learn on.
Anything tall enough to require climbing or a bucket truck, anything close enough to a structure, fence, vehicle, or power line that a mis-judged fell could hit it, and anything requiring rigging to lower sections in a controlled way is a different category of risk entirely. A falling tree or a dropped section that damages a roof, a neighbor's fence, or a power line is an expensive mistake — and if it injures someone, the liability is real and personal, not covered by a homeowner's policy in the way people assume. This is exactly why professional tree companies carry commercial liability insurance and charge accordingly; it's not padding, it's pricing in a genuine risk they're absorbing on your behalf.
Before hiring anyone, ask to see proof of general liability insurance and, if they're climbing or using a bucket truck, workers' compensation coverage. An uninsured crew that gets hurt on your property, or damages your house or a neighbor's, can leave you holding the bill even though you hired them as a contractor.
Many municipalities require a permit for tree removal above a certain size or for protected species, and any job near power lines may need utility coordination before work starts — a licensed local tree company will typically know both and can pull the permit for you. See the permit basics guide for what to check before you start.