EOCF met me at the property with the CEO, their architect, the asset manager, and their real estate agent. 

My personal opinion is that the value of leverage is really dependent on the state of the capital markets... i.e. where are interest rates and is debt working for me or against me? At

Its a manageable game for me at this time and I have a different strategy to "go big".

My question is:Here in Chicago, IL (Cook County) can I use the architectural plans that the seller already has or do I need to hire a different architect to have new plans drafted?

@Chris Cook said it well with checking Airbnb and VRBO listings in an area and you’ll get an idea of where or what buildings allow it.  

I have my fathers pension which will be available to me at the end of the year, should I wait then and get something bigger? 

My fiancé and I want to start our investment portfolio with STR’s and are focusing on the areas listed because of their proximity to us and the attractions that would bring in tenants (Cooks forest, Allegheny national forest, Ohiopyle, Hocking Hills, and all the attractions of the city).

He works at Castle & Cooke Mortgage. 

At the same time I'm not looking to hire a team around me at this point in time. 

That should put me at about 15-20K of my own money once I cash out.