I believe if people make money and there is sufficient housing supply, housing will become affordable. 

It isn't really any harder to drive a stick, just different, but for people who never learned it seems very challenging.

Challenges?

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.

I spend extra for the the supply house versions and rarely have issues during warranty period.

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. 

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

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.

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