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Microsoft is really throwing money at search lately. Bing is everywhere (Colbert, iOS 4, "Filomena", "Search Overload").

How long can they keep it up for the returns they're getting?

Decades. They're Microsoft.

And it's nothing new. They've been throwing money at the web and trying not to fail for years. No real success yet though (IMHO)

Only have to for a few more months until the Yahoo! deal is completed.