i'm in the process of exchanging out of an existing property, and into a large multi-family value-add syndication through a TIC structure. the syndication team is looking to refi their acquisition loan approximately 2 years after the acquisition to return investor capital. the business strategy calls for a sale in year 5. any one out there able to opine as to whether the cash-out refi would fall under the 'step transaction doctrine,' and thus be a taxable transaction for me?

Hi Daniel,First, it is concerning that you are using a CPA that does not respond to you in a timely manner.It would be a taxable event because what you described is essentially a sale of your mother's ownership interests. 

- What is the taxable property value now?

The requirements of the safe harbor election for small taxpayers are: Average annual gross receipts of $10 million or less; andOwns or leases building property with an unadjusted basis of less than $1 million or less; andThe total amount paid during the taxable year for repairs, maintenance, improvements, or similar activities performed on such building property doesn't exceed the lesser of- Two percent of the unadjusted basis of the eligible building property; or$10,000 (for questions about how to calculate the unadjusted basis, refer to "Figuring the Unadjusted Basis of Your Property" in Publication 946You make the election to use the safe harbor for each taxable year in which qualifying amounts are incurred.

Be very careful when you are trying to structure things purely for tax avoidance.If you add your son to the title, you made a taxable gift to him. 

@Jon Passow a lot of it would technically come down to the tax return (i.e. if you were losing money on paper you might not have a taxable amount in either state).

You will have to get the property appraised at the time of distribution to determine it's value and the amount of distribution will be taxable event unless you are taking distribution from Roth and have met the requirements. 2) Non-recourse lending means that the borrower does not provide personal guarantee for the loan, the underlying asset is the only security for the loan.3) You can contribute into an IRA independently of your 401k contributions, assuming you are eligible based on your income.4) If you set up truly self-directed Solo 401k plan you can invest into virtually anything except collectibles and any transactions involving disqualified person.

So many of the variables in your analysis would be people and their opinions on value and where the market is going.As you mention, after tax cost is a concern as your rentals may be generating taxable income however your rent is not tax deductible. 

Nicholas, it actually got amended to 23% deduction.The wages reference only matters if your business pays wages, and your taxable income is over $500,000.

The bill reads "if the average modified gross income of the taxpayer for the taxable year and the 2 preceding taxable years exceeds..."