I am not able to offer much financial support or knowledge regarding strategy.

So this one the City would in no way support the continued duplex use...So the final answer to your above question likely depends on the story, and also likely depends on what the City's preferences might be. 

I am located in University Village/Little Italy. 

Hey Joe, First I'm impressed with this community and how supportive it is.

@Anthoney Hanks thank you for the support! 

The "workmanship" that we're seeing, across the board, is nothing short of disgraceful - paint hiding rotten siding, vinyl flooring over rotten sub-floors, "new" shingle roofs over 2 old roofs where the structure can't support it, load-bearing walls removed with no structural replacement, even a swimming pool that was buried.  

Supporting the claim that our city is growing and there is a demand for housing, even with more units available.Toledo is also the home to many employers.

Purchase price: $90,000 Cash invested: $18,000 Condo close to Auburn University that is currently rented by graduate students.

There is literally not a single comp to support their value.

As long as you aren't thinking that you are going to buy a 2-4 unit property every year and build a portfolio of cash flowing houses in 3 years to support you, then you will be happy.