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.