It's all in how conservative you are in your approach to underwriting your deals.Even when a Seller says they've improved the property, the tenants are still tenants and do damage to brand new improved units. 

I definitely want to align myself with a good brokerage and start building good reputation. 

(NY counties are generally quite expensive)Do you have home owners insurance to cover fire or other damage?

In your example, $250 in utility bills is much cheaper than $2500 to fix frozen-pipe damages!

I retired from ortho in less than 10 years bc of solid investments but he will be forever the loser DB with a garbage reputation peddling info you can easily find on your own. 

It's mostly Class A properties, a few Class B.You may find the below copy & paste info useful in addressing your question:----------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Unless the medical condition meets the state criteria for early termination and that the medical notice does not appear to suggest that, you cannot terminate the lease outright/immediately but that you will begin to market the property for rental and upon securing an acceptable tenant, the lease can be terminated pending a satisfactory property walkthrough indicating no damages. 

In the event you do have to pay for the repair (although I would heavily contest this with the contractor) I think its fair to charge the tenants with an explanation that you did incur damages for the repair although you previously believed that you would not 

@Martti Eckert here's the big issue that no one really talks about that you hopefully find helpful (this is copy & pasted):-----------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

As a would be individual landlord with just a one unit single family property I don’t know I can stomach the risk or withstand a financial assault resulting from an eviction process for a non-paying tenant (or tenants that do extensive damage).I am seriously considering bowing out and selling.