Paying higher than 0% lets him enjoy some of that interest income at lower taxation.

@Michael Martorella , There are a couple of CPA's from New York that specialize in real estate taxation.

What if we kept track of hours but took it as contributions to avoid the double taxation?

Passive real estate losses will not shield your business income from taxation unless you qualify as a real estate professionalHow will the contributions impact your 20% pass-thru deductions? 

@James Findley And who better to be in your corner with the IRS than the Black Belt in Taxation himself!!

Federallaw prohibits state taxation of some types of retirementincome including pensions as well as income receivedfrom nonqualified deferred compensation plans if theincome is paid out over the life expectancy of the personor at least 10 years.

Since your husband is 59.5, early distribution penalties wouldn't apply, but taxation still would.

- I understand estate taxes will come into play once I "pass on" my portfolioC-Corp- Can avoid the 30% tax witholding for NR aliens- Possible double taxation when taking money out of the company through dividends/salary- Shielded from estate taxesI'd love to consult with someone that could talk me through the advantages and disadvantages of each and help me set up the appropriate structure given my situation.

@Jesus Ramirez Income from wholesaling is treated as active income, subject to self-employment tax in addition to regular income tax (at ordinary rates).An LLC is one option but your entity structure should be decided after a full analysis of your situation by your CPA and attorney.

We're obviously not CPAs either, because the $500K exclusion from long-term capital gains taxation hadn't even occurred to us.