I've contemplating looking into those areas as well, but since this will be our first foray into rentals, I figured it would be best to keep the property closer until we feel more comfortable.  

These are the scenarios that I have been contemplating so far:1. 

With all of the run around i am contemplating on just purchasing cash.

I have a few RE quandaries that I could use some help with and I wasn't sure where exactly to start this post but I suppose this can serve as my BP introduction as well :-)  By way of introduction, my wife and I own a townhome in Northern Virginia (6 min. walk to VRE station) that we are contemplating selling (more space, expand family, etc.) but we're not in a position to sell right now.  

In the meantime I'm contemplating testing my skills at wholesaling and flipping.  

I am contemplating the idea of purchasing and rehabbing a property and selling it offering financing. 

I'm contemplating selling one of my rental properties.

I'm seriously contemplating north lawndale.  

I have been strongly contemplating: Milwaukee, Chicago, Indianapolis.

It pretty much summarizes the main points you need to think of as you make your first foray intro multi unit owning. http://www.biggerpockets.com/renewsblog/2015/05/13...All this is to say, we did exactly what you're contemplating and purchased a multi unit via FHA and feel very fortunate to have done so.