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.

You can also expect increasing HOA fees, and there may be some problems renting a property inside a difficult.You don't have any experience, prices are at an all-time high, and rates are also high. 

When the ROE is significantly smaller than my CoC return (based on initial investment) I know it's time to make a move to increase the velocity of the money.

I have clients who are increasing their cash flow by between $19k and $55k and their cost basis is between $145k and $200k.

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

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.

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

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.

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.

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.