Over the span of 5 years you will have paid $77,220 towards rent.However, you're $22,500 downpayment invested into the S&P index fund at our assumed rate of 10.13% compounded annually will be worth $36,236.48Leaving you a net living cost of $36,236.48 - $77,200 = ($40,963.52)Overall numbers after 5 years of house hacking:Expenses include: Principal, Interest, Taxes, Insurance, Repairs/Maintenance, and Private Mortgage Insurance.You will have paid $164,239.76 towards your principal and interestYou will have paid an estimated $20,914 in property taxes and insuranceYou will have paid $5,400 in private mortgage insuranceYou will have paid an estimated $10,859 towards repairs and maintenanceFor a total expense of: $164,239.76 + $20,914 + $5,400 + $10,859 = $201,412.76However, here are the positives to your net worth: Appreciation, Loan Paydown, Rent payments from TenantsYou're home will have appreciated to an estimated value of 560,7812 an increase of $110,782You will have paid down your loan by $26,742Your tenants will have paid $154,439 in total rentThe total benefits add up to: $110,781.87 + $26,742 + $154,439 = $291,962.87House Hacking net worth boosters minus expenses = $291,962.87 - $201,412.76 = $90,550.11(The home equity for year five is calculated using the downpayment + appreciation + loan paydown)House Hacking Vs RentingHouse Hacking net worth after 5 years: $90,550.11Renting net worth after 5 years: ($40,963.52)Leaving you a net worth benefit of $90,550.11 - ($40,963.52) = $131,513.63Here is a screenshot from our calculator on the difference in monthly payments between Renting vs House HackingThe winner is clear.

They told me no tax returns and its financial statement based lending on commercial side, curious if they need to be done by CPA?

So if I setup an LLC, setup a self directed 401k, transfer money from traditional IRA into the 401k, use that to take out a 401k loan of $50k, how does that work with crossing streams and tax conflicts? 

Your refi options depend a lot on how you filed your taxes the last three years.

Should I just forget the LLC altogether and "sell" the property to my daughter, so she might be able to take advantage of any future capital gains taxes? 

If he is working full time on real estate you’ll qualify as real estate professional for tax purposes.

I'm using sites like airdna to help analyze deals but would like a little tip on how to navigate local licensing (if needed or not) and how I could maybe start one in Madison specifically what hoops I need to jump through?

I am in the process of filing taxes.

On your cash flow are you subtracting out what you pay yourself/benefits for you, taxes?   

I am very interested in learning whatever I can so please guys any tips or advice you can give to a newbie, I would be very grateful!