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In place upgrade of sqlserver from 2008R2 to 2014

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Windows server 2008R2 is installed in 64-bit operating system, and there are 88 databases in this server and several jobs and server objects. It might be a complex task to do a side by side upgrade to 2014. Since they are on VM's I was thinking if I could create a copy perform upgrade and test. Can anyone share any experience of in place upgrade on a complex server?

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