I can suggest some other areas as well depending on where you guys are looking. 

Success depends on finding properties in less restrictive areas with strong year-round demand and aligning your strategy with local rules.This post does not create a CPA-Client relationship.

Depending on the location and the city, these could take a long time.

Why are people going for $10M or more, which is at the point you'll have trouble spending it all. 2m isn't enough to retire on, depending on how old you are.

@William Causey depends on the transaction and the parties involved.Agree with @Dennis McNeely on some of the transaction costs.A different issue though is with an Assignment, the buyer gets to see what you paid for the property.

If they are changing jobs, they need the new job first and you need to paychecks or offer letter with salary or maybe even the first two paychecks at the new job, depending on their level and income.Ask them about deposit and rent. 

Depending where your rental is in Chicago, you should also be flexible with your requirements.

ADUs can significantly enhance your property's value by adding living space that can be used for rental income or as additional living quarters for family members.The increase in value from an ADU can vary widely depending on several factors such as the size, quality, and functionality of the ADU, as well as its integration with the main property.

. # of times you talk with your CPA/tax planning (generally tax planning is going to cost more)It depends on the CPA, location, etc.

Otherwise, you can never attain financial freedom because rents will not outpace inflation.How long your rental income lasts depends on job growth in the investment city.Non-government jobs are inherently temporary.