If I use reward points for the flight/hotel/rental car, am I able to apply the value of those points to my taxes for the travel?

Talk to a tax professional.

This puts us somewhere between 18-27mo pending sale.Land Acquisition: 1M + 50K in closing costsHard Costs:Demo: 50KConstruction + Architectural Plans (survey, topography, permitting included) = 1.6M + 80KPool: 100KSoft Costs:Appliance package: 50KFurnishings: 75KLandscaping: 20KAnnual Carrying Costs (utilities/property tax/maintenance): 45KTOTAL: 3,025,000.00 After speaking with two lenders, it seems the best course of action would be to put 20% down on land for 12mo/interest only.

How much tax prep does a bookkeeper do? 

If I sell it outright for cash, does it invalidate the entire 1031 exchange or do I just pay tax on the 25%? 

I'm the Tahoe Reno, NV market where the taxes are lower and more landlord friendly.

Does anyone have any good recommendations for a tax professional that knows real estate/multifamily/airbnb?

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.

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

My broker assured my property manager they will receive the same coverage as before, however internet articles claim  additional insured  "is not covered by the polity for any liabilities arising out of your business.""