If you spend time learning how to manage well, your income will increase, you'll save time, and you'll maintain your sanity with the courage to expand.

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 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 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.  

In some homes planting the front or placing pots could increase the curb appeal, in others it could be paint or furniture etc.

If you want to keep the architectural attractiveness of the house, it usually runs a bit more expensive.  

As I am new to this and looking for cashflow using rentals, one key aspect of this investment is to ensure that the unit rents out quickly and while I do understand that cash flow to begin with might not be attractive, it can be a good investment in the long run if the location is right(as appreciation also kicks in).

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

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

Nothing attracts buyer leads like houses for sale.