If you have time ahead of you then bleeding money every month for that eventual big payday might be good.

@Jason Arcuri I hear what you're saying, I'm just looking at the overall financial picture of the state of Connecticut, and the fact that the state is bleeding citizens and businesses at an incredible rate, and I have to ask myself how many renters are there going to be when the overall population is trending down rapidly, and the fiscal situation of remaining citizens is either not going to be good, or is going to be good enough that they can buy, not rent.

Other "damage" that we've had to use funds from this account to pay for were small things like a new coffee pot (when the lid was melted in the dishwasher), a new set of sheets that were damaged by a wet bathing suit bleeding red dye, and a new twin mattress when a special needs child accidentally wet the bed.We've collected about $34,000 in damage wavier fees by now.

So you buy for appreciation but you can't make mortgage payment because you lost your job and your property is empty or bleeding by negative cash flow.  

Quote from @Joe S.: Well, this is not a normal tenant and this is not a normal rental. 

She said she's had hives, swelling in the face, feet and tongue.

Small town for sure but swells to the second largest city in the state for 20 weeks :-)

If they do not come up with the money, which is likely, at least you have stopped the bleeding and can free up your rental to another tenant whom can pay.Also in the future do not return a security deposit and then rent to someone else in the family.

I assume the home is in a Cleveland suburb so I speculate it isn't appreciating as fast as the loss.If bleeding money is ok, how long should it occur?

He cleverly got around it by bleeding some of the heat from the apartments into the halls so the tenants heat the halls and they pay their own heating bills.