I would love to Dm you and get your number down send some deals in Chicago your way in here near future 

@Timothy Frazier Yes, the only reason to use HML as a down payment is if the property is "mostly turnkey" AND you don't have the funds to renovate AND you have strong CMA comps from a real estate agent that supports that the fact that you are buying a property that is under valued AND your renovations would push that so that you could refinance.

I've just  been brushed it off for a while as I continued to build a portfolio on own, and wanted to continue to gain more experience before going down that road and the large responsibility that comes with bringing in other peoples money into the investments. 

By the time I reach 20% equity (likely 3+ years away), my monthly mortgage payment will come down when I refinance, but $600 is a big hit to the numbers. 

A good broker should be able to tell you a range of rates given specific criteria if you can tell them what kind of deals you are exactly looking at (ex. in central Boston, 10-20 unit, 90%+ occupancy, 30% down).

I would suggest taking the route of option 2 or 3, so not only are you saving over 10k in rent per year but the residents help in paying down the debt.

Cool, what are you focusing on to pin down which investment strategy you're looking for?

You won’t get the metrics like the pay down or the returns on the second note this way but you can get the accurate cash flow.

Concentrate on your development cost and keeping them down and the deal will pencil.

I haven't seen the City crack down on unpermitted work with regards to a LTR rental license but that doesn't mean it won't be an issue some day.