I want to break the cycles I've learned about money, owning properties and investing.

You would need to find a non-appreciating market where rents are high in comparison to home prices to at least get a 2% rule, even though you will probably break even or have negative cash flow due to interest rates.

Of my 25 total reservations (not including cancellations) 2 are from VRBO, 4 are from Booking.com, and the other 19 are from AirBnB. 

It is a balance sheet of all of your assets and liabilities including both personal and business. 

Some will be passed on to the tenant.You can include non-recurring expenses such as capital expenses, repairs, etc. 

Sister's rent amount, term (date of refinance), mortgage payment responsibility, insurance responsibility, utilities responsibility, tenant selection responsibility (since this will be a multifamily property), property management responsibilities including repairs, maintenance...2.

No, the vast majority of business's, including service business, start-up's do NOT clear profit day, month, quarter, year 1. 

It usually ends bad for all involved including the GP.

I am planning to do refi in April/May time frame this year, hoping to get Appraisal for up to 150k with 80% LTV making it a break even deal and also considering the rental estimates(1600/month). 

The most you can lose there is 3x the deposit and the court costs (a few hundred $).Even a slip-and-fall lawsuit won't break the bank.