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

I notice that you comment on almost all Roofstock related posts usually to defend Roofstock.

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.

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.

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. 

Then the owner of said program would respond defending his/her program.

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?

. • Documentaries: Check out The Queen of Versailles for insights into the challenges of hotel investments. • Podcasts: The BiggerPockets Commercial Real Estate Podcast has episodes on niche asset classes, including hotels.