Oh, man, this made me recall the "borrow, then die" strategy mega rich people use to avoid capital gains taxes:
* Step 1 is to have a large investment portfolio.
* Step 2 is to get a loan from a bank against that portfolio with a sweetheart interest rate, very long term, and interest only payments with a final balloon payment.
* Step 3 is to let the dividends and appreciation on the portfolio pay back the loan.
* Step 4 is to die, leaving the entire portfolio to your heirs. This gives them the ability to take advantage of the step up basis, so they pay no capital gains should they sell, which also gives them the ability to immediately sell a portion of the assets to pay off the loans. They can then go on to implement this same strategy themselves.
There's not a direct mapping between this and the "held-to-mortality" book, but the spirit is certainly very similar. While it's losses being hidden by banks using the "held-to-mortality" book strategy, it's gains being hidden by people using "borrow, then die." In both cases, it's essentially done by delaying realizing those losses/gains until as late as possible.