Upon your passing, your assets that pass on to your heirs will be valued at a base value equal to the appraised value at the time of your passing so if they sell the assets at base value, they don't have to pay tax - essentially your estate is tax free up to ~$11 millions. The only exception is regular IRA/401K, it will be considered as ordinary income to your heirs and will be taxed accordingly.
No, you're fitting the date to the idea that buy-and-hold might be a bad idea. You basically give half the picture... It all depends on when etc.... Your statement that it's bad since from the late 80s they are down (which is factually correct), gives the following chart. Vs long term reality.... Up from 200 to 22000 now, with top at 40k. Or vs a shorter term from 2010.. up 110%...
New IRS rule: Beneficiary has to start withdrawal every year based on his/her life expectancy and the amount is taxed as ordinary income. Please check with your tax accountant, I am just a layperson.
If you start in 1989, and you invest like us small retails, put in a small amount every month, reinvest the dividends, by now your return may not be too bad.