You are the business owner, you are responsible for all employees and contractors. You can't expect an assistant to put up with the low pay and long hours AND, by the way, if you break something you bought it.
Having to pay for accidents is another reason that photographers have to keep their rates at a reasonable level. Far too many photographers only think of the direct expenses of the individual job they are quoting and totally disregard the "hidden" future expenses such as this. When I get push back on prices from clients, I remind them of things like insurance, upgrades, rent, taxes and clumsy assistants. All of a sudden that $3,000 quote does not seem that high.
You will need to provide the insurance to cover your equipment, reshoots and people that you employ and guests in your place of business. Accidents happen and you cannot expect the Assistant that you hire as a freelancer to pay for something that you asked them to move. For years, I worked as a freelance Assistant and never would have provided insurance for someone else's gear when I'm making $175-$300 for the day. Imagine if I was asked to produce a Certificate of Insurance to assist a photo shoot, I would have laughed in their face.
Tony,
I have insurance for my gear but as you know you would have to pay for the deductible and your insurance rates would go up.
Do you seriously think that you should ask the Assistant for your deductible? What would happen if the Assistant got hurt on your set doing something that you asked them to do? If you are that concerned, prequalify your freelancers if you don't already.
I recently had an assistant accidentally break a prop, luckily I had an extra one and it was inexpensive but it made me think what if... What if an assistant breaks YOUR equipment on a shoot? Who pays for it? Does it matter if its a $10.00 cord or a $7000.00 camera? Even if you have camera insurance and the assistant does not. Etc.