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

The fix-up and increased value will not matter to the IRS as long as you sell within a reasonable time frame of the house passing into the estate.

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.

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

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.  

BUT, I am sick living in construction and would like to move to a new home and then finish fliping and sell or hold the two homes asap.

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.