@Matt Smith - as @Christopher S. mentioned you cannot use an ADU unit in Chicago as an AirBNB as the city's intent with the program is to provide additional affordable housing. 

I mean, he probably wouldn't describe it that way, but that's what he was doing.It takes time to grow organically, and it is frustrating and painful at times.

Now I’m looking into the Detroit and Ohio areas (Toledo, Cincinnati, Cleveland, Columbus) since they seem to have growing populations and affordable properties under $200k as well.  

You want to have your financial house in order so you know what you CAN afford and what you SHOULD spend.

Custom vanities, large format tile showers. 24x48 marble look ceramic seems to be affordable and look incredible. 

For me it boils down to more of a personal decision - can I afford two homes, do I want to have two homes and the stress of it, or just take my money out of one and put it in another.

Strengthen Your ProposalDevelop a Business Plan: Include:Vision: Your goal of creating a micro-home community.Market Research: Show demand for affordable or small-footprint living in your area.Financial Projections: Break down costs, ARV, and anticipated ROI.Experience: Highlight your previous fix-and-flip and demonstrate your learning curve.Present a Solid Development Plan:What is the size and scope of the project?

So now an employer has the affordability to afford the coach/teacher manager and the over-sized staffing.

Amazon has an amazing selection of affordable covers and you can search by color/pattern.

why not build in a more affordable price point. the largest two builders in America build non luxury maybe take their advice?