You'll benefit from leveraged appreciation over the next market cycle. 

I imagine after a couple cycles of renters we'll get a feel for the demand level of different features (since we also plan to do exit surveys to get that kind of input).Just to clarify we also meet pets to determine temperment, take pics of pets, charge a $500 pet fee (non refundable) and pet rent of $25 per pet.

As with all large cities Chicago has submarkets which go up and down with cycles. 

If so and it didn't sell, it is into the REO back cycle of the process and they will just wait for it get listed by their chosen REO broker.

Lots of investment grade tenants have been around for 40 to 100 years so have made it through economic cycles.

Can't wait to see what this cycle brings.

When a paycheck is on the line, miraculously everyone knows how to get the job done, or who can get the job done, right?

They are informative and provide a lot of insight, such as how long the average property stays on MLSbefore it is sold in that area.Additionally, get familiar with the Real Estate cycle, for example, whether it's a buyer's market or seller's market, and how local factors affect sales prices.

Also, this is something you often do on a schedule (like you make it part of your X-year maintenance cycle), and you could just say that to tenants...Which relates to the other thing you do, which is spread it over the X years, and just tell the tenants that it's part of CAM even when they sign.  

While market rent is great, these tenants do cycle through your houses causing extra costs in repairs + vacancy time in between tenants.