Please clarify, how many lenders we have "signed up" and how much they "pay" for "leads".

I'd also add to that that you are paying a 20% withholding tax on gross rental income. 

They're less than I pay.

I'm being required to pay another application fee and then $600 application fee to hopefully get this approved by the Board to allow me to continue running the STR that they approved 6+ months ago. 

Use a quitclaim or warranty deed to transfer the title, and be prepared to pay Chicago’s transfer tax, calculated at $7.50 per $1,000 of the property’s fair market value.

G'Day Alejandro,As a few have already mentioned, take a peak at Toledo also.In my opinion lower potential for long term appreciation but solid/"boring" cashflow.I prefer my portfolio to be "boring" but cashflowing lolLow entry points (Sub $100,000), high rents (Above the 1% rule).Blue collar working class decent folks that will stay and pay.Depending on the area but no derelict homes, yards well kept, cars with wheels and all tenants are employed.Plus, all are sophisticated enough to pay rent online so property management doesn't have to collect rents with bullet proof vests and shot guns lolI'm bias toward Toledo but it's worth considering.Wishing you much success

However, aside from that, I couldn’t find much information about them, and the only online presence seems to be the wife’s LinkedIn profile (though I’ve never met her in person and am just going off her profile picture on Zillow).After submitting the application through Zillow, we attached our income (two months of pay stubs for each of us from our current jobs), work references, credit and criminal background, rental history, and the contact info for our current landlord (who just so happens to be my fiancé’s father).

In return, they will be motivated to get a job and pay back every dime owed while lavishing you with praise.

A tenant not paying has nothing to do with us either.

You don't need to pay anyone to learn.