The older houses were built with Florida pine which is hard as a rock and won't take a nail without drilling.

Yet they do well because of volume and he fact that people have been renting cabins in the mountains for as long as a hammer and nails has been around.

@Pedro Bartolomei@David Ribardo Hit it right on the nail.

I know its fun to talk about saving peoples credit but by the time the foreclsoure is filed its in the toilet . once it sells its simply another nail in the credit coffin but they are already 5 feet under ground so to speak.  

Realtors and investors need to mitigage risk while marketing their properties...one photo is not enough but you don't need 20 to generate interest while preserving privacy.  

Sell the property with inherited tenant to a bulldog who can deal with the tenant who is entitled to you treating them to a massage, craft beers, acrylic nails and hair to be done every week.

I have my strategy set and calculators warm but struggling to nail down a fast but reliable way to estimate expenses when assessing a lot of potential props.  

His income/expenses tend to transfer from property to property, so it has been challenging for me to nail down my underwriting assumptions.

Yes @Emma Hans is exactly right and it sounds like you already know; Ithaca is bizarrely specific when it comes to code enforcement, historic preservation, and a bunch of other things that seem to make little sense.

BUT BUT BUT let's address a key thing here . . . it seems like you may be getting the cart before the horse.I'd highly recommend finding a savvy CPA (one that self-identifies as a tax advisor would be even better) that is competent in real estate, then getting coffee with them and your favorite asset preservation attorney and pepper them with questions.An LLC is a liability protection play and NOT a tax play.