Once I figure out a few markets I am interested in, I plan on establishing a relationship with investor friendly agents in those markets.

I also plan on house hacking once I’m more financially stable and renting out the second unit of a multi family property.

You stated once a variance was denied, new plans were approved and permits issued.

Despite new reporting requirements, such as those imposed by FinCEN, it's still possible to achieve a degree of anonymity with careful planning and the proper jurisdiction.

I can tell you right now, between using hard money debt as you plan and the inefficiencies of managing the types of markets I suspect you are chasing, you aren't paying down principal either as you will be continually refinancing.

I personally invest in areas that there have development plans for the future knowing that I will likely gain appreciation from the investment.

Are you planning on investing in any particular neighborhood in Chicago? 

I am currently fixing up a few things and plan to get into a conventional loan (within 12-24 months) via a cash out refi and put that equity into funding my next property.

Our plan is to subdivide and sell off lots to pay off the loan and keep the rest for to develop as short term rentals or an event venue.

A refinance was never part of our business plan for this one.