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

The best advice I can give you is to rent for a year.

Cincinnati, Ohio does not have any extra rent taxes.  

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

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. 

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

I am specifically looking to rent out to section 8.

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?

They can use alternative rent models (STR, MTR, rent by room, etc) to increase cash flow. 

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...