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This paper looks at both the strategic benefits and the strategic challenges of moving to Cloud and SaaS for mid-sized businesses, using insights developed from more than eight years of SaaS and Cloud research among user executives by Saugatuck Technology. It will provide insights regarding SaaS and Cloud IT, and examine the pros and cons of two typical approaches to both. Throughout, it will provide insight and guidance regarding key decisions to be made regarding how to transition to Cloud IT, including the value and risk inherent in selecting not just solutions, but providers.