They're less than I pay.

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

Risks: rates go down and you have to pay a prepay of 2 or 3 %; you have to sell and pay the prepay; rents decline & you can't make the payment like any other type of loan; cost upfront a little more than conventional; need to find experienced broker licensed in the state where subject property sits; servicers are bulldogs. 

If you have large debt with a high interest rate, I would consider paying that off before getting started investing in real estate. 

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

Bottom line: the tenant doesn't get to decide how to pay you.

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.

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

A longer timeline will make paying the extra 2% now more attractive.

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