My interest in LTBH investing in growing, however, and frankly I'm beginning to think that the problem is not that I'm worried about valuation, but that I'm just not all that used to taking taxes into account in making investment decisions. That is probably where I should be focusing my planning efforts. I don't mind paying taxes, but I don't want to feel like a fool for doing it.

I know some people who let the tax tail wag the returns dog. A tax inefficient good investment is usually better than a tax efficient bad investment. But tax is certainly a real thing.

My usual reminder to people unduly worried about realizing gains and paying tax by switching investments half way through one's savings life: remember that even if you pay a big chunk of tax, you're not losing that money, you're paying it sooner as you'd have to pay it eventually anyway. (barring some country-specific exception cases).

The loss from paying tax on a realized gain (like a hundred billion worth of Apple stock?) is not the amount of the tax which so many people focus on, it's only some time value of that tax amount, which is generally a much smaller number. There is a big difference between losing a million, versus paying out a million 10-15 years earlier than you otherwise might have.

Jim