Good luck collecting anything from them. My family has been down that road, won lawsuits greater than 10k for rent and damages, etc, but you can't get blood out of a turnip.
Going forward, enact changes. Why was there 1500$ unpaid rent and no eviction? The security deposit seems very small compared to the rent owed. Consider increasing the deposit. Upon collection of rent, can you collect the checks in person on site and check the property yourself (or management to check?)
I don't have experience with insurance and collecting anything that way.
Other than that, enjoy your tax loss on the property for the year!
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