Now I have rented out once which was not successful and have paid a lot in taxes and the property is regularly broken into. 

I will also add that we repair items immediately on the STR that we may let go for a while on the LTR (example, broken fence planks, paint (STRs get painted as soon as they show some signs of needing it, LTRs we try to only paint at tenant turn over)).The humidity at the beach may also be a contributor.   

You get your milage summary broken down by personal and business via emails.  

Nothing about a journalism degree qualifies one to opine or editorialize on brain cancer or mortgages, we kind of have a broken system in that way...

When I came back, my trash can had been stolen and strangely replaced with a totally broken one with holes.

You're an even ether candidate because if you're not insured, you could even settle out of court since you could pull cash out and payoff that poor guy with the broken head and his caring brother in law.I recommend having an umbrella policy that regardless of the amount covered by your real estate properties', covers you for at least the amount of your net worth.

Such as, an identified item like a broken door, a hole in the floor, the roof or something specifically disclosed by seller would be AS IS. 

Quote from @Sam Faas: That sounds right, but I am not a fan of this technique because you are agreeing to return the deposit "without condition" and they could choose to leave the place dirty, abandon broken furniture, or just trash the place on the way out the door.I have done something similar, but I offer to return the deposit within 72 hours as long as they leave it empty, clean, and in good condition.

A few broken shingles here and there, curled up shingles, damaged skylight frame window.2) Mold noted on the basement walls. 

From the description (and my brief googling haha) it sounds like the NOI broken down for a period.