I’m not trying to make this sound transactional, but there are so many elements within marriage that can impact a completely different department, and it’s significantly harder to make big decisions when other areas seem off.

Having the ability to amass capital is one of the key elements to getting successfully involved in REI; but it is not a get rich quick venture.

The cost for vendors to travel that far would be excessive to the owners and result in a whole new set of vendors that you don't get a chance to interact with often, again resulting in either higher cost or poor service.

Either way, you will need to interact with a lot of folks and you will want to educate yourself on the Chicago Land Lord Tenant Ordinance as well as fair housing rules so you don't do anything to get yourself into trouble. 

@Diana CosttaYou can Promote Your Property with a local Real Estate Agent.Generally, real estate agents understand critical tidbits of this industry as they routinely interact with property developers, tenants, landlords, property managers, etc.

If I could slightly hijack this (or add one additional element to the discussion)...at what point would you consider a PM? 

To be more successful, you simply have to work on the other elements to progress your REI pursuit.

I don't know which jail he is in and have yet to speak to the chief interactively to get more details.

Since your interest lies in buy and hold, I added the below links for your review.http://www.biggerpockets.com/renewsblog/2013/01/04/how-to-rent-your-house/ (house rental guide)http://www.biggerpockets.com/renewsblog/2013/02/22/buying-rental-property/ (how to buy a rental property)To be more successful, you simply have to work on the other elements to progress your REI pursuit.

As such, for a high-interaction asset like STR, you will need a property manager.