You can use a co-borrower just make sure they have good credit and a (2) year work history of W2 income.Try and avoid self employed co-borrowers because their tax returns typically do not show income and are full of deductions.

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

You can also build a relationship with a good local agent and ask them to run comps for you, or in certain situations like selling a high-end home to a friend off market I’d recommend just paying for an actual appraisal.

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. 

I feel the same as he does.Here's what helps me in those situations...figure out the plan if things don't go according to plan. 

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. 

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. 

We have 3 airbnb’s in the Tampa/St Pete area and property taxes with insurance is reducing our returns.

You'll just be sitting on a ton of equity with no tax benefits.