Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

We remediated what could be found sent pictures jumped though all the hoops and they still said they weren't going to renew.Got a new policy that has a 25k deductible just to make the premiums tolerable.

I just acquired it and would like to report this property on Schedule C to deduct the loss of first year operations and expenses against my other Sch C business(es) and my husband's W2.

Hi Luke, an education expense is a deductible business expense only if you get the education while your working in a business with a profit motive. 

A checklist or detailed description of move-in condition is required to deduct anything from the security deposit. 

Yet, because of the deductions, I pay almost nothing in taxes.4.

The fee they are charging you might be higher than the limit set in the law; the law might not require you to provide a copy of the lease; and they might not be able to assess, levy or charge a fee or fine or otherwise impose a requirement on a member's rental property any differently than on an owner-occupied property in the association.

I've heard that the Sarasota County is in need of money (and that's the reason AirBNB deducts taxes and directly passes them to the County) - how strictly are those rules enforced? 

@Levi Collins: As long as the tax deed clears title process, that should not be an issue.

Were any of the repairs something that should have been deducted from the previous tenants security deposit?