The problem with these strategies is that most of the fonts being used are from places like FontDeck and TypeKit, and are paid for by the impression (or a monthly/annual license fee including X impressions). That means that the font requests are tracked (and requests have increased latency) and aren't cacheable. Actually purchasing the font for unlimited web use (something that's normally prohibited in the font's standard usage license) can be godawful expensive compared to the foundry's monthly plans, at least over the short term (1-2 years).
This is really just cost analysis, though. Page speed is money at some point. There are foundries that will sell you Web font licenses for dozens of dollars; unless there is a specific need for a high dollar font, it is very possible to do it on the cheap.
Designers are picky, but the boss pays the bills at the end of the day, and chances are he will settle for a slightly different font if it saves him thousands of dollars per year.
