Realistically you would expect the house to continue to appreciate during that time as well... even if at 3.33% appreciation - that is another $50,000 in appreciation you would make in the 3 years - give or take.  

Educate yourself on how to house hack.

I’m hoping that once I do have enough saved I can buy the second property and continue house hacking.

Are you looking to make being a chicago real estate agent your full time job or just a side gig while continuing to work full time? 

Even if one has to provide the education to some of the parties as to why a particular creative solution makes a win-win-win for all. 

We have been working in the affordable housing space for some time, and this allowed us to partner with the local community and provide a housing solution they need as their city continues to expand with new jobs they are successfully bringing to town.

anyone have any experience with Walter Wofford and his short term rental education programs?

WIll Trump continue the support?

Therefore, your financial freedom hinges on new companies continuously moving into the city, creating replacement jobs.Companies have many options when selecting a location to set up operations.

I'm reading books and listening to podcasts and such but having someone I can shadow is a more valuable educational experience.