However, this home is in Berkeley and I am concerned about destroying historical elements and potential added structural engineering costs that could make the house attractive to a buyer in future years, along with the opportunity cost of construction now versus getting rental income from the house in the next few months. 

One town-wrecking tornado destroys my entire portfolio.

Your mediocre tenant turns a year later, destroys the place and you have to put another $2500 in.

Just trying to avoid someone destroying my house during their last month here as he rents a room.Thanks.

We'd have never seen the money anyway even if we'd won but I'm still salty about that.In the mean time, her dogs (we’re a pet friendly rental) have totally destroyed the place even beyond the quite nasty conditions she was living in, even after she had been living only a week in the unit so far.

Sounds so wrong to pay off a bad tenant to leave but is probably 5 times cheaper than booting them the hard way only to find your assets destroyed.  

Well there is a bad  time to invest, if one don't have the experience and  one could not borrow/obtain cash for reason or another, greed and overconfidence are bad to human, if someone would like to invest in daily basis without enough knowledge and cash will at the end of the day will destroy him financially.

BIG MISTAKE.Those horror stories you hear about houses getting destroyed…that happened.

Also easy to replace a small section when a tenants destroys a plank.Take a look at the flooring they sell at Costco. 

Go ahead and destroy the cash flow completely on the one you plan to hold.