Ideally, my dream is to have a condo in my favorite neighborhood of Chicago (Lake View).I'm 24 years old.

Hi Nirek - I deal with a lot of clients in your similar situation.

Our biggest problem is getting her out so we can do a proper rehab 60 days of dead dime waiting for her to vacate is not Ideal obviously. 

@Jeffery Jones As someone who owns 6 single-family homes under the Section 8 program and runs a property management company that manages over 100 Section 8 properties, I’ve learned a lot about the ins and outs of the program—not just the idealized version often shared on social media.If done correctly, Section 8 can be a great way to diversify a portfolio.

Same process as always, BG check and proof of income as most of the property owners I deal with require.

I think it's ideal for a 1031.

After living in the property for a full year, we have come to terms and accepted that this is not our ideal location.

We did not do this and still encounter less than ideal setup the result of our initial setup many years ago.  

@Elvon Bowman Do you have an example of the ideal property or a price point?

A 4-plex would be ideal and you could play around with doing 1 long-term, 1 mid-term, and 1 short-term, plus you, if it works on your area to upgrade your income.