The roof had a tree fall onto it, and subsequently the house has water damage and mold.  

Trying to estimate maintenance, tenant damage or eviction expenses is impossible.

Our lease document does state any cleaning costs, unusual wear or damage...these things would come out of the security deposit.

You have tenants in there and the basement floods, I can envision scenario's where they will want out of the lease, damages for ailments, and even ask for you to pay for a hotel room for them.Now, this does not mean that you are obligated to do any of those things but you are potentially setting up a rental that may be more of a headache than it is worth.I have walked through many homes and written down: NFFAs in, Not For Free.I would advise caution with a flooding problem that is not resolved.

Foreclosing and reselling a property for much less then a previous short sale offer, having "Property Managers" managing properties they no longer own, allowing REO agents to give "pocket deals" to friends at 50% of market value, not fixing minor leaks that lead to extreme water damage, etc. etc.

Failing to close on your behalf is considered damaging and thus the escrow funds are forfeited.

In the three years since I've started purchasing properties (I have three close to home that I self-manage) I've never had a single late payment, and have only ever had $50 in turnover costs for damage (not including vacancy as a turnover cost, although I've actually only ever had about 1 week of vacancy.)

The HUD property the appraisers use the minimum for documenting damages and issues and do not take into effect resale values or flipping etc.

. :)BTW, if the job is not completed, fire him, hire another and who cars how much it costs to finish his work, as he is responsible to the bid price and other damages if he walks off the job.

Landlord was found to have breached the agreement and was held liable for damages to the tenant.