That will most probably be offset by an increase in new mortgage costs and increased rates. 

They'll tap out in 3 months, max.Rates can increase.

The home in mn over 20 yrs averaged 2.8% increase per year.

You can add different ways to reach out to improve your conversion for owners you are hitting or you can increase the amount you are sending. 

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.

I would be cautious buying in the saturated areas because there are so many similarly sized properties that price is becoming increasingly the deciding factor. 

Quote from @Paul Lucenti: Creative methods tend to increase risk.

If this property is hard to rent, or is functionally obsolescent (only 1 bathroom, no yard, etc), or has deferred maintenance that will be costly, or is in a location that is not appealing to Tenants, then maybe a sale would be a good option in favor of a property that has better Tenant appeal, which will likely increase rent and avoid long vacancies in between Tenants.An option to consider....

As the years have progressed, I've seen a healthy combo of appreciation & cashflow has continued to increase as market rents have gone up.To start off, I'd attend some local meet ups and network a bit, and start analyzing some deals.

The end product will be great, as others have mentioned perhaps in other threads, Delta has not increased any of the cost, so there is still a huge equity upside.