Personal Injury Law
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It is impossible to give you an exact number, if you are found responsible (you might have some defenses described in your fact scenario), you would be responsible for his medical costs, pain and suffering, and possible punitive damages (this is unlikely). If the tenant has an affirmative obligation to keep the property clear if ice and snow that might be reason enough to not be responsible although you as the landlord would be responsible for maintaining certain areas. In New York, a property owner/possessor is required to maintain/repair their property in a reasonably safe condition. If someone is injured due to the failure to maintain the property in a reasonably safe condition, then the property owner can be held liable. At the same time, every person is responsible to act in a reasonable manner for their own safety. The failure to do so can result in the injured party, and not another, being held responsible for their own accident/injury. New York is a pure "comparative fault" State- meaning cases will not be dismissed solely because a defective or dangerous condition was "open and obvious", but that fact will be left to a jury to decide who bears what percentage of fault for the happening of the accident given that circumstance - the injured party or the property owner. That is why you can get different results in different cases. (the jury can find the injured party 100% at fault; the property owner 100% at fault, or distribute the percentage such as the 50-50 you noted). So you should probably retain a New York personal injury defense attorney to ascertain your chances.
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Having his own rental insurance is no factor, although it is possible that he could put a claim in with his own insurance but that does not release you from liability if you are in fact considered liable. The lease does not protect you if it is something you are responsible to maintain. I'm not saying that this might not be a legal defense, but it does not preclude the tenant from filing suit. Like I described in my first answer, new York is a cimperative negligence state and it will be a question of fact to the jury how much you are in fact liable.
Just checking back in, do you have any further questions?