, 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?

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

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?

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.

For newly constructed, purchased or renovated properties and also retroactive generally over the last 10 years, building components are properly classified into individual units of property and accurate recovery periods for computing depreciation deductions.

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. 

I am currently in the processes of getting my real estate license and don't have accesses to the MLS, despite this I still want to practice doing comps on housing in my area to better understand what makes a deal great.

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

Info pulled off MLS directly.We are now in that time of year where school has begun and, cyclically, real estate cools down for a little while.