Once you do your first deal it will be so much easier for the second one.  

I have owned hundreds of rental houses. and other than deposit or eviction issues.. have not really felt that we were a target.. for one thing the average tenant has little to no money and therefore cant sue you.. and these cases are not taken on contingency UNLESS they think there is insurance money to get.But I get the sentiment..

It makes a life a little bit easier on whoever is doing the title work in the future. 

Maybe someone will act on it and buy, This kind of activity keeps the price up and makes it easier for local investors to sell to OOS entities. 

Is there some simple math that would make our decision easier?

But the more assets you have the easier it is to get one.  

I think I would target a duplex or quad plex that needs a little fixing up. 

It could be anywhere depending on your budget, what is your cash flow target, type of property you are interested, type of the renter you want to deal with etc....Almost anywhere in Baltimore can cash flow

@Michael Starks  Also, I would try and determine your target market.

The longer you do it the easier it gets.