My concern would be that once you have done the in-place upgrade, it will be tricky to go back and do a 2nd pass if any problems or rework comes out of UAT or Go-Live . (unless you use VM Saved States / Snapshots on your Servers if they are virtual) So if you are doing a Test Upgrade before the Live Upgrade, you would need to repeat the upgrade process at least twice - would could be slower than having a conveyer belt of 13, 15 and 16 servers waiting to run through the upgrade. (as once you have the 'conveyor belt' setup, you can bosh your Database through quite quickly) As the jump to 2016 is quite vast for Training and Testing, would definitely recommend having a solid process of upgrading a UAT/Test Environment first to then let your Users or Client loose on 2016 before gaining their approval to do Live. So I think both approaches should work, but think having a set of CRM Servers that you can repeat the upgrade on would be more sustainable.
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