But ya have to make some educated prognostications in life.Add this to the information your processing - What your talking about doing is eliminating around $4000 or interest expense (which is deductible anyway so really could be a real impact of eliminating $2800 or so) of debt in exchange for paying over $10K in capital gains tax (don't forget possible state gains tax as well).  

More likely, he is hoping to use the extra time to collect more rents and thus more fees to generate the funds to pay his owner clients:(

Say they sold the properties over 3 year period and could not sell the rentals together as a portfolio.Could they put the money from each sale into a DST then use the total to buy a expensive rental property?

Grow wide first, then deep (pay off)- your little expenses add up fast

Set aside a big pile of cash or rely on a line of credit you won't be using.The oversimplified insurance concept is to pay a small premium to cover a large loss.

Was that a past career in sales, management, or something related to real estate?

If you achieved this by paying all cash, then you are losing money. 

If you already have existing property and transfer property to an LLC, then it could trigger the due on sale clause the bank.

When so many renters stopped paying rent during COVID, companies like SureVestor stopped taking new accounts because they were facing a significant number of claimes.I personally don't see it as a good solution.

But it had been for sale on the market since July, 2024.