The insured cleanout vendor wants $2,850 and the two guys with a truck want $1,400

The disposal piece is the one I'd chase before the insurance piece. I had a lot dumped on and the city came to me, the owner, not to whoever backed the truck up. Rules differ by state and by county on how far liability follows the waste, but the pattern I've seen is that the land owner is the easiest person to find. So the question I'd ask the $1,400 guys is which transfer station and can I have the ticket. If they say yes and hand you tickets, most of your gap closes. If they get vague, that's your answer.

Put a number on the thing you're actually buying. The gap is $1,450 on a $19,000 spread, so 7.6 percent of the deal. You'd pay that premium if you thought the chance of a bad outcome times the cost of a bad outcome exceeded $1,450. A dropped-fridge back injury claim against an uninsured helper isn't a $3,000 event, it's a five figure event minimum once anyone involves a lawyer, and how it lands depends on state law and on your own policy language, which is a question for your agent and not for this forum.

So the math works at maybe a 5 to 10 percent chance of something going wrong. With two guys carrying appliances out of an occupied-then-vacated house, I'd put it higher than that, because that's exactly the job where people get hurt. Also check what your own vacant property policy says about contractors on site, mine has language I didn't notice for a year.

A few plain definitions, since this thread turns on them.

A COI, certificate of insurance, is a one page document from a vendor's insurer showing what coverage they carry and through what date. The two lines that matter for cleanout work are general liability, which covers damage they do to the property, and workers compensation, which covers their own people if they get hurt. You can ask to be listed as an additional insured, and you can ask the insurer to send it directly rather than taking the vendor's copy.

Workers comp is the reason the two prices differ as much as they do. Comp on manual labor is expensive, and a crew operating without it has a lower cost base. Whether you as the property owner can be reached when an uninsured worker gets hurt depends on your state's law and on your own policy, so confirm that with your insurance agent in writing before you decide, not after.

Disposal is separate. Ask for the transfer station or landfill ticket as a condition of final payment. It shows the load was weighed and legally dumped, and it gives you a paper record of the job.

On the personal property left behind, states set their own requirements for handling abandoned belongings, including notice and storage in some cases. Ask a local attorney what applies before anything goes in the trailer.

The version I'd write is neither of your two options as they stand. Take the $1,400 crew and make them a documented vendor. One page: scope by room, the price, tickets required before payment, a line saying they're independent contractors carrying their own coverage, and a clause on personal property that says anything with a name or a document on it gets set aside and photographed rather than hauled. Then get them a COI or accept that they don't have one and price that risk yourself.

If they won't sign one page, you learned something for $0. If they will, you're paying $1,400 for the work plus your own hour of admin, and the thing @ledger is pricing at 7.6 percent gets a lot smaller. Contracts don't stop injuries, they just decide who argues what afterward, and your insurance agent is the one who can tell you whether the paper actually helps in your state.