I don't like the idea of being the owner of a "dangerous" tool that they may injure themselves with nor do I want to deal with repairs of such small items.  

Many of the arguments for hiring insured contractors suggest that you'll want to place a claim on their insurance rather than yours when something happens (e.g. they get injured on your property).

If the individual is working alone and would be covered medically if he were to get injured is it reasonable to go with him? 

Also, if someone is injured on your property due to the negligence of the tenant and they have no coverage/assets, who do you think the Attorney will sue?

If someone injures themselves and sues, they will be suing the LLC and not you personally.

Now if one ever gets injured it's another nightmare.

If someone injures themselves and sues, they will be suing the LLC and not you personally.

Make sure you have an umbrella insurance policy to protect your assets in the event someone is injured/drowns in the pool.

If someone injures themselves and sues, they will be suing the LLC and not you personally.

If there is a slip and fall or some other liability issue, the injured party is going to sue the landlord and the property manager, so your insurance company can protect both of you in the same claim.