As a SharePoint consultant past 6 years I have performed various SharePoint Upgrades.
My experience shows that typically the migration road map looks like this:
Want to take a peek what were actual challenges and discoveries of SharePoint upgrade?
You are more than welcome to dive into it!
Upgrade from SP2007 to SP2010
Upgrade from SP2010 to SP2013
Manual migration from on-prem to SPOnline
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