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I've been using it almost exclusively for as long as it has been available, and I'm a pretty intensive user. The only outage I've encountered was a planned one a month or two ago, and I got plenty of warning. Can't say the same about MobileMe, with a much larger budget! I've also seen plenty of apologetic tweets from Dropbox saying that yes, their service is down and their provider is working on it. If the OSS goes out, you can just point your software at a different WebDAV server and continue to work in the same manner (albeit without access to files you had only on the OSS), whereas when Dropbox is down, you've got to switch to an entirely different way of working if you've been relying on Dropbox as your file conduit.

Nothing different happens during the sync to the OSS vs. the sync I would do to Apache running on my iMac, but the support ninjas have tools where they can quickly see the sync activity, etc. and they can repair the database if it comes to that.

Marginal cost to supporting OmniOutliner, OmniGraffle, OmniGraphSketcher, OmniPlan is probably vanishingly small; it's all just standard WebDAV traffic, and they built the server infrastructure for OmniFocus.