The investor must consider whether the potential property value increase or other benefits outweigh this loss. 

Chicago is a lower appreciation market but with the trends we've been seeing with increased rates of hurricanes on the east coast and fires in the west, I do think long-term we will see some migration to the Midwest.

It was a 50% of one months rent and a $100 increase in rent. 

If Oak Park allows STRs, leveraging that history could make the property stand out.That said, unless the home has been preserved as a landmark or has unique historical features, the value boost may be more about novelty than a significant price increase.

If you have a high level of faith in the company you are working with, then time will do what it is supposed to do and increase your IRR.  

I like the cash flow and see the potential for increasing rents, but I’m hesitant about overpaying.

Materials have increased more than 20% in the last 5-8 years.

In 2022 the rents increased 12.1% year over year which was the 3rd highest in the entire country per https://www.axios.com/local/cleveland/2023/02/14/cleveland-rent-prices.

Also keep in mind as time goes on typically your yield will increase because of the rent growth. 

Our monthly mortgage payment would increase, but we would still break even.Both of our car loans have an interest rate of 4.5%.