Congrats on your success so far.Some random thoughts for you:- It might be difficult to tap the equity in the rental at this time given the current state of interest rates. 

Even at a high cap rate you've got several million dollars of market value here, so I'm curious about your base numbers.

Crickets...At this rate, it will be 2+ years before the project is finished.Anytime you ask for a project plan or schedule you will get vague responses with no actual plan.

My original plan was to find a 4 plex in california buy using fha loan, move out after the first year and generate cash flow and appreciation, but after looking at properties it became clear to me that’s not possible with todays market and interest rates.

Is it high appreciation area with a low rate mortgage?

They are short term loans, usually 6-12 months, high rate, interest only payments. 

With insurance companies canceling policies and raising rates has anyone uncovered a way to self insure rental properties?  

Also the hit rate per property is really low.

Chicago is a lower appreciation market but with the trends we've been seeing with increased rates of hurricanes on the east coast and fires in the west, I do think long-term we will see some migration to the Midwest.

They will take the permit fee and send an inspector that will provide some assurance that the work was performed correctly.