She wants to put proceeds into a strategy that is not real estate, which obv presents challenges for tax mitigation.

An eviction will make it challenging for her ever to find a quality rental in low vacancy areas.  

Sidenote: if borrower is paying P&I and investors receiving interest only it gets more challenging as you are receiving dribs and drabs of principal back every month which is impossible to deploy but you are still paying investor interest on it. yup drag on the fund will drag you down.

The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

But, they will be in challenging parts of town where realistically you do not want to own property and your long-run returns will under-perform.I'd encourage you to find a balance of sub-market growth, nearby employment, strong income, and only then a good rent-to-value ratio. 

and I gotta tell you it's really fun to get to see the impact of my legacy gifts while I'm still around to watch my children prosper.  

.: Hi there,I have an investment property in Atlanta and over the past year, the property had major challenges due to squatters.

The more you say, the more they can challenge you if it comes to that. 

or “What has been the biggest challenge for you as a new investor?”)

Challenges?