Oklahoma as a whole has strong rental demand in many markets, just need to be mindful of the price-to-rent balance, as you mentioned.

I know Air/VRBO are strongly pushing for hosts to offer non-cancellable bookings at a 10% discount. 

If you feel like you have a strong argument, you might as well try it's the way I look at it.

.- Creative Financing: Partnering with other investors, seller financing, or using HELOCs can help scale your portfolio faster while preserving your capital.- Land Development: Got an eye for raw land?

The rental market is strong due to students and digital nomads.Managing a couple of tenants would not be too hard but managing a dozen, on the other hand, would be a nightmare.I am a bit torn.

I have strongly considered managing on my own in the past. 

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Quote from @Rodney Davis: Has anyone done a deal with this company, Strategic Investments Partners? 

We don't allow any "deal-making" in the forums, which includes advertising your services or properties, looking for partners, etc.

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.