@Derek P.If you are looking for cash flow, then this may make sense especially if your retirement investments are not performing well.You will want to review the Roth IRA distribution rules:https://www.irs.gov/retirement-plans/retirement-plans-faqs-regarding-iras-distributions-withdrawalsYou will want to review the 12 month 401k loan rules as well.

The question comes as to when or how we might go about taking distributions.

Beware of pretty appearances, non standard building techniques, aluminum wiring, newspaper used as insulation, lath/plaster walls, piece-meal additions, real 2”x4” (not 2x4s) and square nails.

Apartment Complex) using leverage that cash flows for 2-3 years before being sold due to appreciation and distributing the gains from the sale proportionately to the Syndicated LLC members.

I'm looking for clarification as to what are the IRS reporting requirements for pass-through income which is distributed through a land trust to the beneficiaries? 

See the following.https://www.irs.gov/retirement-plans/plan-participant-employee/amount-of-roth-ira-contributions-that-you-can-make-for-2018Also, earnings on non-deductible IRAs will be subject to taxes once distributed.

What tends to happen in white collar careers is that those who are most adept at taking advantage of new technology will distance themselves from those who don't, and there will be a bimodal distribution of talent. 

Amazon has (4) distribution centers here, the Port is spending 424 million on dredging to 50 feet, the logistics business is crazy nuts here in Jax. 

I know the LLC mechanics, but tax is still a bit above my head.]Hey @John Woodrich - from tax perspective, do you have an opinion one way or the other if @Jon Loca did the following:Dad deeds property over to LLC, for "consideration less than $500" to avoid hefty deed tax when recording.Dad invites his partner-son to become a small part-owner of the operation of the business that is this rental property by buying into the LLC for "services to be performed"Lender like @Tim Swierczek helps get the property refi'd under the LLC, with cash distributed pro rata to the owners -- does that get ordinary income, or capital gains treatment?

Your money now is not serving much value and would be best distributed among several properties in the form of minimum DPs.Taking a HELOC and paying it back to reuse again is a much slower process that has no advantage.