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Lumifer comments on Money threshold Trigger Action Patterns - Less Wrong
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You are asking good questions, however your original argument, that Americans don't ask them because discussing money is taboo, is hardly correct. If you take a society where people openly discuss theirs and each other's salaries, savings and budgets, all the same questions remain.
Oh, and as for the concept of ownership in general, it almost never makes sense unless you love both the concept of owning something and the thing you own. Renting a boat is cheaper and less time-consuming unless you sail daily. Tying your funds in real estate for non-business/investment/tax purposes only makes sense if working on your place brings you joy. Owning cars only makes sense if you are willing to drive an older model and/or like to tinker, otherwise leasing is cheaper and more flexible. Note that most other items on your list are not ownership: an insurance policy, donation, hired help etc. But that's a side point.
I disagree. I think that ownership provides a number of significant benefits not all of which can be straightforwardly converted to money. One benefit, for example, is control over your property and the associated freedom to do with it what you want. Another benefit is reduction of risk in uncertain and turbulent times.
Ownership of which things reduces risk, though? If you own a fishing boat, now you're vulnerable to additional risk (damage to your boat, the constant threat of big expensive repairs - 'a boat is a hole in the water you throw money into'), and you no longer have the resources you have spent on ownership of it up front rather than renting a bit at a time; those were resources that could have been a cushion against risk. If you spend $20k on a fishing boat & all its many expenses, you're now down $20k and up on risk; if you keep your $20k, well, $20k buys a lot of protection.
A valid point. Ownership is not an unmitigated blessing :-D and there are certainly trade-offs in play.
I am not saying "you should always own if you can", I'm just objecting to shminux' "almost never makes sense" -- I think it makes sense considerably more frequently than "almost never".