Serious question: how do these work, and can you actually make money off. or can you only limit cash losses with them?

Only as a last ditch attempt to preserve some business assets and wipe out debt, after exhausting all other options to raise cash, improve sales, refinance, issue equity, restructure, or other normal business operations to keep the company operating.

And no, those six bankruptcies were not strategic, they were failures to operate a business. One bankruptcy is strategic, two a coincidence, six a signal of incompetence. The sheer number of shell corps he's founded and thousands of civil court cases points to exploiting investors through shady practices.

One strategy might be to start with a number of business entities; move "troubled assets" of all entities into a single entity and have that entity declare bankruptcy.

You have multiple businesses, and sell assets between them... then bankrupt the lame ones.

Example: Business 1 buys a $1M piece of equipment with 30% down and 70% credit. After a couple years, and knowing that Business 1 is not that profitable anyway, the machine is sold to Business 2 for $150k, even though it's probably worth $700k still.

Business 2 makes $550k profit on the books. Business 1 files bankruptcy. The creditor loses their $250k outstanding loan. If the same owners own both businesses, they come out massively ahead.

Rinse / repeat with dozens (or hundreds) of businesses, some automated workflows and depreciation tables, credit line hacking, etc.

Can't the bankruptcy trustees come after the owner when they see that the machine was sold far below value? They do something similar in personal bankruptcy.

Selling things below value is pretty typical in a liquidation/bankruptcy scenario, though.

Yeah but there are limits. If I'm about to go bankrupt and I sell my $700k house to my brother for $150k, the trustee isn't going to let me get away with that.

Those limits are dynamic based on connections / how many white shoe lawyers you are willing to fund.

An established real estate family will have plenty of room to shuffle assets and credit lines around in a favorable way within those limits... for a generation or two.