To answer the question in the title, you should look at the purpose of the study. The study naming Singapore as the most expensive city come from the Economist Intelligence Unit's Worldwide Cost of Living Index, which is supposed to "help human resources and finance managers calculate cost-of-living allowances and build compensation packages for expatriates and business travellers" and is "based on the assumption that an expatriate has a right to live at the assignment site in the same manner and with the same kind of goods and services he would find at home" (source: https://www.eiu.com/public/topical_report.aspx?campaignid=Wc..., http://www.worldwidecostofliving.com/asp/wcol_HelpWhatIsWCOL...).In other words, it's comparing the price of living a Western executive lifestyle, not the cost of living for a regular person. Transport costs are high because Singapore has very high taxes on cars (more expensive than the cost of the car itself) - the target audience isn't going to be using a bus pass. Food costs are based on prices at high-end Western restaurants, not $5 worth of groceries. The housing comparison definitely isn't based on a studio apartment. And so on and so forth.
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