If Anyone has additional information on the Chicago market right now and some insight Id love to talk. 

Marketing Strategies:In addition to listing on major platforms like Airbnb and Furnished Finder, consider joining local Facebook groups for military families or relocation services.

After a couple of years of treading the path to frugality to build this financial runway, I've networked with the greatest people who made this all happen, of course, it took the strength, determination, time, etc to place myself where I am today but, without the mentorship of my two great mentors whom I wish used BiggerPockets so I can mention, I don't believe I would have made it thus far relying on some whimsical dream that this will all pan out accordingly, thank you for everything Greg and Lashawn.In addition, I would like to thank Bigger Pockets for connecting me with the greatest realtor @Stephen Schmitt Who took my dreams and aspirations to the core when we first connected and spoke about my future goals to replace my W2 job for financial freedom. within three months of me deciding to pull the trigger and get pre-approved, we found this killer cash-cow that apprised over purchase price!!! 

I'll echo what Zeke mentioned about interviewing multiple realtors / PM's / Contractors to make sure you can get a good idea of what the area is like, in addition to working with someone you're comfortable with. 

These are professionals with additional training and a stricter code of ethics.

$800k at a couple extra percent means it’s costing you AT LEAST $16k PER YEAR in additional interest.

I was drawn to real estate as a way of investing money I have saved up (around $130K with additional funds to leverage out of a 401K if needed), and potentially creating reliable cash flow over the next 10 years. 

In addition this fire storm started when payments stopped or payments were returned to the bank NSF.

The property title is clear but the lender wants additional property adjoining to cover the roof overhang rather than just an easement or encroachment.

Contact a couple contractors to see what the cost would be to add the addition.