If you have a older home that has never shown signs of foundational issues, and it has a new(er) roof, electric, plumbing, HVAC, hot water heater, etc.

If they suspend/lose their license, they're dead in the water.

I also own a water restoration and general maintenance business in the area and the amount of STR owners that we have spoken with is insane.  

So it takes comprehensive knowledge of the market trends, zoning laws, the local municipalities approval process, survey cost, subsoil conditions, irrigation requirements, development cost, utilities (gas, power and internet), city water or well water, city sewer or POSW to name just a few...A builder developed the farm field next to our SD, bought it for $1.5M and wanted to build 25 homes as a conservancy subdivision.

You also mentioned an unpaid water bill, so be sure to deduct any outstanding balance from that bill as well. 

Water in the plumbing system freezes at 32.

The city required the road to be extended a few feet, along with water and sewer.

Many people have a mortgage on a property where the land value is much greater than the home (aka near the water) and insurance is not able to pay off your entire outstanding mortgage.

@Jennifer Fernéz I run sum numbers for you with our tool, see comments and pics below before refinancing and post refinancing .Financial Breakdown: Purchase Price: $200,000 Mortgage (LTV 80%): $160,000 Interest Rate: 6% (30-Year Amortization) Mortgage Monthly Payment: $959Upfront Costs: Down Payment (20%): $40,000 Closing Costs (3.5%): $7,000 Renovation Costs: $15,000 1 Month of Carrying Costs During Renovation: $1,548Total Upfront Required: $63,548Year One Rent: Monthly Rent Income: $2,000 1 Month Rent Losses during renovations (-$2,000): -$167/month distributed over 12 months Total Rent Income: $22,000 per year => $ 1,833 per monthMonthly Expenses: Mortgage Payment: $959 Property Tax (Assuming $3,000/year): $250 per month Property Insurance (Assumption): $100 per month Utilities (Hydro, Gas, Water): $275 per month Assuming 5% Vacancy: $92 Assuming 0 % Repairs & Maintenance first year because unit has been recently renovated Total Monthly Expenses: $1,676Monthly Net Cash Flow: $157Post-Renovation Refinancing Strategy after 12 months:So far, we’ve purchased the property, completed renovations, and rented it out.Next, you can approach the bank for a refinance to consolidate a portion of your initial investment into a mortgage.

Just starting out and testing waters for BRRR in Chicagoland area.Any advice or suggestions regarding this?