That could be a good solution if the properties are good and rents are good to not lose the cash flow.

The rent is not realistic with the bed/bath count and the condition;it needs a large rehab.  

It might be more useful to set your sights on the reality of today and tomorrow and end of the month.Things such as learning to collect the rent, learn to place good renters in the property, etc...

In Milwaukee, I'd need 2 exits from the attic and 50% of the space has to have at least a 7 foot height on ceilings.Two things you want to check: both requirements are correct, but on top of that the city is getting reluctant permitting 3rd units: 50% more occupants mean 50% more water and sewer and 50% more traffic and parking.The other issue is that the cost of finishing a thrid floor with proper insulation/ventilation will run about $50-60/sf and only makes sense if you can get strong rents. 

Cincinnati, Ohio does not have any extra rent taxes.  

And you need local knowledge to find the professionals and get a sense of market rents and values.Any Florida agents out there that can help @Bob Asad?

Looking for guidance on best neighborhoods/areas to consider in order to Buy, Renovate, and Rent in Philly.

It is a 2/1 Duplex where I will live in one side and rent out the other.

I would also try to raise the rents of other units before the sale will help you sell it at the highest price.

I am specifically looking to rent out to section 8.