Hey @Jon PfluegerFirstly, great initiative to ask this question.

I’m especially interested in house hacking as my first investment since it seems ideal for building cash flow, reducing expenses and gaining experience without heavy initial capital.Questions & Market Focus:I'm still learning, but I’m starting to research these four markets to understand which may be the best fit for house hacking.

You cannot finance more than what wouldve been available in the initial purchase or use any improved value or new appraisal to increase the loan amount. 

This creates two loan payments ($100,000 of equity and $300,000 on the new mortgage).Key NumbersHome Equity Loan Interest Rate: 6%Mortgage Interest Rate: 7%Rental Income: $3,000 per monthExpenses (management, taxes, insurance, maintenance): $800 per monthIncome and ExpensesMonthly Rental Income: $3,000Monthly Expenses: $800Monthly Mortgage Payment: $2,000ExplanationThe investor earns $3,000 in rent each month.They pay $2,000 on the investment property mortgage and $800 on other expenses.This leaves $200 profit each month or $2,400 per year.However, you have to pay $6,000 interest on the equity borrowed.This leaves you with an annual loss of $3,600.While the rental property generates positive monthly income, the interest cost of borrowing the initial $100,000 results in an overall annual loss.

Initial Inspection and Assessment: Document property condition before work begins. 

I would like to update my initial response.

@Michael Plaks Didn't you say you were buying coffee for us at the next one of these "sessions"?

Initial rent was $575 per side.

Initially, all new residents stay for about 6 months in our largest home.

Your initial post was unclear whether the water bill was $2k/month or if the balance was $2k because they weren't paying you for it.