Is it worth taking a chance on a house that is good looking, at a nice location etc.

Just waiting on one of my houses to sell.

My tenant moved out a couple of days ago, and when I walked through the unit, I discovered that he had removed the curtain and curtain rod, detached the room air conditioner, and caused significant scratches on the hardwood floor from the metal bed frame legs.

We focus mainly on value add properties in A/B areas.

So yes, based on what you've posted it sounds like your CPA is correct. 

Any property managers in Cleveland that would take on properties renting by the room?

Currently, I am working on renting out my extra room in my 2 bed, bath condo.

Waiting on owner decision. 107 Ellis st. - DuplexUnit A - 1 bed 1 bath - Updated water heater, flooring in kitchen, kitchen counters, appliances, and bathroom. $875 - Vacant and just listed. 

Could I do itemized deduction on a schedule E as an individual?

Hey Austin, congrats on starting your LLC!