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I am in a syndication that for the first time I am concerned about loosing some of my investment.  

Yes, many times but then we cover rent until renovated and tenanted.Have we had an investor loose money on a deal?

Your HOA will likely keep increasing and because of the excessive heat, roofs get replaced more than in other areas and if the HOA is not super liquid, that will come back to you in the form of an assessment.

If there are excess losses, Citizens can surcharge all policyholders to help pay for the claims.If you have a long term rental, it is a viable and affordable option, but it should never be construed as the best option. 

The 1920s in Florida was a time of excess, immense wealth, and precipitous collapse.

Complicated rooflines, modern details that require a bunch of steel framing, excessively large great rooms, spa-like bathrooms, etc would push you into the $1,000-2,000 range.  

Whenever I read investor posts about unit count goals and utilizing section 8 rentals as the vehicle to scale a portfolio it loosely translates to buying real estate without paying attention to the fundamentals in the markets where they invest.

I was loose with my description.

My tenant of 1 year just moved out recently (work transfer), but during the move-out inspection we found that one of the 10X10 bedroom has all four side of the wall covered in screw holes from the time they used it as a computer room (I believe the holes were from the sound deadening foam that they used to attach to the wall) So I was wondering what would seem to be a fairly reasonable cost to be deducted from their Security Deposit for the excessive holes and needing to repaint.