Your absolutely correct that we all have different perceptions of "extravagance"

I think a vacation to hawaii from portland for a family of four while still in debt is clearly extravagant, and unaffordable. But's thats just my opinion, and I dont expect you, or anyone else, to share it.

Debt shouldn't be seen as ok to have but I think that is sadly how most Americans view it now.

Depends on whether the Portland in question is in Maine or Oregon, and whether the trip was an extravagant package or little more than a cheap-deal flight and minimal accommodations. At a glance http://www.cheapflights.com/flights-to-hawaii/portland-OR/ shows a flight package of $1548 for 4. Camping, hostels, or - here's a thought - Craigslist might open some cheap options.

According to anthropologists, debt appeared before money. So it's hardly a new development that debt is seen as OK.

Mortgage? Student Loan Debt? (OK -- I know you American's have crazy prices for University and thus crazy loans)

Do these pass your muster? A lot of people still view these forms of debt as acceptable.

The problem isn't debt but debts that aren't paid back. Debt itself serves a useful purpose. As long as he's able to service his debts under the terms agreed upon, the rest of his money is his to use as he pleases. I don't think we know enough about his finances, like the cost of the trip, to be able to say that the trip was clearly unaffordable.