Also, forgot to mention, this house is a hundred years old! 

Cash flow has not been easy to get in the last few years due to the appreciation home saw due to the Pandemic.

I’ve been investing for 15 years with rentals, flips and BRRR.

, is this something that would be offset if you just hold the property after a 5 year estimated proforma with a 3% appreciation/rent increase?

Do I take a chance on a property that may not cash flow for a few years?

Cook County Property Tax Incentives: Cook County has a tax incentive program that allows projects to receive a special property classification for a 12 year period that lowers annual property taxes by as much as 50% through the term of the incentive program.

Our question is, once we do this, how do we recoup enough funds to purchase a second property sooner than a few years from now?

I've been retired for years now as a full time LP.

I agree the cleaning and maintenance is more challenging to me than the administrative but there is a sizeable segment that are opposite.Also @Nathan GesnerAirbnb smart pricing and being on 2 platforms only is not comparable IMO to over 20 channels now and having a Wyndham trained revenue manager with 12 years experience. 

After 4 years of paying landlords rent, I would like to start in investment real estate.