So more Roth for way less in taxable income incurred. doing this is easiest in a Solo 401k if you qualify but can also be done using a checkbook IRA as well. check out this post that @Dmitriy Fomichenko made explaining this concept.https://www.biggerpockets.com/forums/51/topics/1223601-how-t... 

So your super basic P&L may look like: $30,000 Rents-$3,000 insurance expense -$9,000 interest-$3,000 taxes-$8,000 operating expenses-$14,000 depreciation ----------------$7,000 loss on paper for the year  so negative taxable income But remember- $14k of that (depreciation) was something we didn't actually spend money on- so cash in bank at year end would be $7,000. 

As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year. 

Under the assignment of income doctrine, income is taxable to the person who earns it, even if it is directed to someone else.

This could reduce your taxable income in those years.Your decision depends on your long-term strategy.

The IRS won’t allow this as a legitimate deduction.No Tax Benefit from Self-RentEven if you set it up through an S-Corp (which is more complicated), the rent payments you make would be taxable income to the S-Corp.

Exchange now at 500k over basis into income property with lease back and put option for 300k more. 

First off to be clear when using income for these screening purposes its GROSS income (before taxes).

There are several things that come into play with determining if a property sale is capital gains or ordinary income. 

If I do, I need income to get me to 59 ½ because I can’t access my retirement accounts until that age.