The major philosophical obstacle to Cloud Services is that of ownership and personal control. Many people and organizations, perhaps even the majority, will continue to keep their data and services in-house rather than relinquish that to the fluffy white entity in the sky.
This is particularly true where Microsoft is concerned because it has built its reputation on freedom in computing. A shift to relinquished control is a marked philosophical shift, one that people will not readily adopt. Members of the COA (Cult of Apple) will gladly use the Cloud because they've already given up computing control on a persona level. Not so with MS.
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