They could use the tax break for gifting into someone's 529 and I wouldn't claim the money that goes straight into the kids 529. 

Is it better to buy a primary house with 5% down and stay for 2 years after which I can rent out (hoping rents increase by then) if not I can sell it and be and be exempt from taxes on capital gains.2.

Using a 1031 Exchange we were able to defer capital gains taxes and upgrade to the VRC.

If you have or buying a rental/airbnb or even fix and flip.  Do you want the property in business name/LLC etc?Also if you have a business for just buying/selling land only and spend money/milage traveling to properti...

You'll pay:6% or so in RE sales commission: $20,400Payoff of a 216k loan to lenderRecoup your 40k for loan costsThat leaves 63,000Short term gains tax 40% (25,200)You net 37,800. 

You've built something up to the point where you don't want to lose it, and house hacking is a phenomenal entry point with incredible tax benefits. 

If he has properties, look them up on the tax records and see.

When you price out the Principle interest taxes insurance and any HOA the rents in most states won't cover the payment unless you have BIG down payment or equity. 

For the purposes of calculating the limited interest deduction, the total mortgage debt owed would include both the individual mortgage on Unit A and the owner's share of the underlying mortgage.So, the total mortgage debt owed would be $800,000 (individual mortgage) + $200,000 (owner's share of underlying mortgage) = $1,000,000.Therefore, the owner would be limited to deducting mortgage interest based on this total mortgage debt of $1,000,000, not just the individual mortgage.Thus, the deduction for mortgage interest would be calculated as:($750,000 / $1,000,000) * $40,000 = $30,000Therefore, in this scenario, the owner would be able to deduct $30,000 of mortgage interest for federal income tax purposes.

He has suggested that to defer taxes I first transfer $150k from my current Roth IRA account into a new Self-Directed Roth IRA custodial account that I will open.