After I joined there was one very specific, honest review by Zach Harsh and boy did he get slandered for it.

But, since you seem to be implying very specific things, but without being specific.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Do you have a specific area of Chicago where you would like to live? 

There is no specific IRS-mandated minimum holding period for a property acquired through a 1031 exchange before you can retitle it, that's why it's hard to find an answer. 

Not sure of specifics.

Rent control laws are market specific.

Any HML will want answers to those questions plus a rehab budget before getting you a term sheet for a fix n flip loan for this property.I close these types of loans all the time, if you have any specific questions about the process don't hesitate to reach out.

Additionally, the frequent zoom meetings help provide new opportunities to learn with the group, network, and get specific answers for your questions. 

Other sites that can be successful included Facebook (specific groups you are targeting like traveling nurses or 5th ward housing, etc), Airbnb/VRBO (30+ day stays) and insurance placements like ALE Solutions.