Many of these areas also benefit from both rising home values and increasing rents.Ultimately, successful investing comes down to selecting a growing market, a strong neighborhood, and building a reliable team to support you.

Market might be competitive but there is angles to stand out depending on what you are comfortable and able to handle, such as waiving an appraisal contingency, limitng inspection rights and time frames, closing time frames, allowing seller to stay-post closing, taking on difficult tenants, buying properties that might need repairs, etc.

Also, as long as the house appraises, taking broker commission and using it against down payment and closing costs means lower cash requirements for me which increases my CoC returns.

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.

as @Marcus Auerbach alluded to, out of state / remote / out of country investing is difficult... do you have everything else lined up?

Just make sure you are saving towards those slow months during the peak months, buy a deal at the right price (don't overpay just because its a turnkey STR or you think it will make more money than projected), and look into ways to increase bookings during those slow months with some marketing and operation tweaks. 

It is harder, more difficult, more risky to wholesale without a license.

., Richmond, and Detroit led rent increases, while Austin and Raleigh saw year-over-year declines due to high supply.

Based on that, do you anticipate increasing or decreasing your investments?

The neighborhood has seen a lot of revitalization in recent years, with an increasing demand for both residential and rental properties.