As stated above it really depends on your personal style and strategy.  

@Jimmy Chao depending on the style lock they most likely used bolt cutters to remove it.

I've thought about a dumpster but the site is quite tight and getting a dumpster would likely mean sacrificing limited parking and this location is heavily car dependent.

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.