I see the point you're trying to make, but I'm less convinced it applies to real estate. For one thing, real estate doesn't seesaw with such ferocity as stocks

I see the point you're trying to make, but I'm less convinced it applies to real estate. For one thing, real estate doesn't seesaw with such ferocity as stocks. Sure, bubbles form and prices crash. But the floor for real estate is that people need a place to live, and population goes up. A stock can go to zero, while a house can be underwater (figuratively, let's hope), which matters if it's financed. Stock options can become worthless, while land very rarely becomes worthless. Buy and hold is an option with real estate, because in general the asset price will at least track inflation at a minimum. It doesn't rot like an overripe banana like in your Sun stock example​, where holding it too long was a punishment. Real estate developers will sometimes take a condo project and turn it into rentals if the market turns before they're done with construction. The reverse can happen, rentals can turn into condos in a hot neighborhood. Those aren't the only elements to consider, but for an illiquid asset real estate is surprisingly flexible, as I'm finding out. Put aside the fact that I can't live inside my stock options if I need to downsize my expenses.