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Punoxysm 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.
Owning a car can have a large advantage over leasing, if you are likely to keep the car a long time. An owned car can also become a second backup car, that it's no big deal if it breaks down) if you get a newer one. Leasing two cars at once is a big waste of money.
Owning versus renting a home is not clear cut at all. Renting a house is a huge money pit unless you are frequently moving, and renting an apartment vs. owning a house is often not comparable in lifestyle. Owning a house gives you the property and flexibility, and can result in longer-term wealth building.
There is a lot of debate in America about whether or not we are still in a housing bubble, but it seems to be the general consensus that in at least some areas of the country, buying a house is probably not a good long term investment.
Do you, by any chance, mean the northern part of America that sometimes goes by the name of Canada?
In the USA, the pre-2008 housing bubble has certainly popped. Now, one can argue that there is another one inflating right now, but I haven't seen many people make that claim.
The Motley Fools have a pretty good, and brief overview.
There are other articles around that name various sets of large American cities that are maybe/probably bubbling, and California is often cited as being at the forefront of the bubble.
However, you are right, the claims are that we are in a new bubble, not the same old bubble.