Moving to version 2016 from 2008 and Breaking Change Alert from Upgrade Advisor
Going from 2008 to 2016 is jumping too far.
I suggest you to go move to 2012 first and then to 2016.

First of all download Microsoft Migration Assistant and try to spot incompatibilities.
Then download Microsoft Assessment and Planning Toolkit and scan for all sort of incompatibilities following a guide.
Spot the incompatible queries using the Query Tuning Assistant

Now that you are on 2012 repeat the steps 1, 2 and 3 and move to 2016.