My experience so far:

For the big company you pay a big chunk of money and they show up on time and are done in an hour or three. The tree(s) comes down fast, everything’s hauled off, chipped up, or ground down. They likely do several jobs in a day, so that’s where the money comes from. You know it’s 99% chance they are actually insured.

The small business consisting of a guy or two might get to you in a few weeks. He might or might not show up for the originally discussed time and day. They’ll be there for several hours, probably take a few breaks, and then they’ll need to drive off and retrieve their chipper truck. Maybe he’s insured. Maybe not. You’ve just got to go by his word. Grinding the stump might happen same day, or maybe a couple days later when they drag the stump grinder around to the last 5 jobs they did to finish them.

The big company will cost more. But not a whole lot more.