Other than a duplex style, what type of small-ish build outs would be affordable but also be most convenient for house hacking or renting out to a tentant without interacting with them as much?

Plus it had a shotgun style layout (no doors between rooms). 

There’s good news regarding your dream to open a Chicago area sober living home is that you would not be the first to do so, & there are literally hundreds of smaller mom & pop style SLH’s in the area that are currently operating & would be more than willing to help guide you through the process so you don’t have to go at it alone (now I sound like a sponsor), also there are numerous Federal, State, City, County, & private grants, benefits, & tax deductions you can receive to help you get started & operating. 

Some things that are going to impact the price of the insurance premium: 1. insured building value 2. building material (frame, masonry etc) 3. age of building 4. roof style of building and age of it 5. number of units in the building 6.

Well, I know for me personally, I often get very frustrated by the market that I live within, as the classic "buy a multifamily and rent out the other units" style of househacking is incredibly hard to find.

Then try and match the colors from there with the style of the house. 

This is something I will look into more in depth on my next deal (i.e. suitability for rent style.

This is something I will look into more in depth on my next deal (i.e. suitability for rent style.

I listed another house one time that was just the opposite....sales price about double the tax value....unique house, unique neighborhood about a block long with all kinds of styles, sizes, ages.Just knocked off 25% of the tax value on an investment property I owned by challenging the value at the appraisal district hearings....value of the house has not changed, condition has not changed....their value was automated and not challenged by the district fairly.Bank appraisals where someone actually sees the house, sees the inside, and is familiar with values in the area is way more accurate.

So decided to get in the market Turnkey style.