You are going to want to talk to several professionals in your state for this one as it is a legal maneuver that amateurs or even professionals not familiar with the details of your situation on the internet probably aren't going to be able to help with much.

They know how to milk more money, in my opinion, and would ask a for a couple more opinions from other professionals in the industry

You will be labeled strange, weird, bizarre, cracked, and stupid until you achieve a measure of success in what you do.

When we do get into to contact the lack of timely professionalism on simple request leads to more frustration.

Readers are advised to seek professional advice.

This means that with a good tax professional and some tax planning you should be able to reduce your AGI to ensure you meet this allowable loss limitation. 

Chicago is major metro market and there are lots of great RE professionals here.

Such as any professional.

I already generally do not wear makeup and wear non-descript yet professional clothing.  

The professional buyers  that own lot's of properties have their own system and attorneys with lenders etc.