You'd still lose money from the original price, but it might be less damaging than a short sale.

So I provide blinds and usually the faux-wood plantation style that are a little more expensive but it makes for a better impression on prospective tenants  and I charge for any that are damaged upon exit. 

You don't want this, (but it is cheaper) with this type of policy the damage you have has to be caused by something specifically included in the policy for coverage to apply.In the end you need to determine exactly what your needs are. 

I have structural reports from 4 years ago that indicate that roots from trees planted against the house were damaging the house.

Phase 1: Demo/Interior Framing layout walls and rooms. [10 days] Demo whole house/clean up interiorExpand walkway between living room to eating are by 3 feet (install new header)Frame up new laundry area, frame bedroom wallFrame up new patio sliding rough opening and install new sliding patio doorFix water damage floor in hallwayTile bathroom floor and wallsInstall rough electrical throughout house.Install rough plumbing throughout house.Install insulation and drywall sheetrockMeasure windows/door.

Then he left his windows open in a rainstorm, the place got flooded, my plank floors ruined and he claimed several thousand damages on his stuff.

You can do all the Smartmove researching and just like with a Stock, one bad Economic news event or like Hurricane Mathew could take a left turn and we have 160 mph winds running up the length of Florida and all the fly by night Home Owners Insurance companies declare Bankruptcy and no one gets paid for damages.

"If unforeseen rot, deterioration, insect damage or poor structure is found and is found that it is necessary to replace the disturbed area, not included in this scope of work, an Additional Work Agreement will be written at such time for such repairs and costs will be due payable prior to work being completed.

I think I read in "The Landlord's Survival Guide" that you don't want your security deposit exactly equal to rent because that gives tenants the idea that they don't have to pay last month's rent and then I'm out the cost of any damage they did.

The damage is done.