This is a unique home and it actually has a full kitchen, 2 bed and 1 bath downstairs and I think it might be well suited as a very large vacation rental(entire home) or both floors being rented separately at some point in time.  

I have 3 windows as well that don't stay in the open position that I have to replace.

You want them all to be able to communicate well with you and with each other.

It very well could become a large enough investment to be worthwhile, also solving for "unexpected emergencies ", for the most part and would an easy self management situation if you were to live onsite in one of your connected townhomes.

I would go as-is as well!

They have always rented them at well below market rate and the repairs were made by the tenants.

If this keeps reciprocating well with the community, I'll keep doing them.

And you can be a landlord that gets a very poor return because they haven't utilized their space well by changing the layout.

Even if you go "vertical", that tends to require an architect as well. 

Here are pockets I focus on for cash flow:West side - West boulevard, Cudell, Clark-Fulton, Jefferson, Bellaire-Puritas, Old BrooklynEast side - Fairfax, Buckeye-Shaker (the north side), Waterloo Arts District, Garfield Heights, Maple Heights, Newburgh Heights, Lee-Miles (the north side), BedfordHere are the areas that I focus on for appreciation:West side - Lakewood, Edgewater, Old Brooklyn, Ohio City, Tremont (above 490)East side - Buckeye-Shaker (the north side), Waterloo Arts District, Fairfax*I have a graded neighborhood map of these areas as well if you would like to check it out.