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.
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.