Hi Andy!
We've been migrating hundreds of thousands of accounts to the cloud for the past 4 years. A few typical lessons to be learned:
* Office 365 consists of many services and products! It's hard to say you're just going to implement it in one step.
* Find your ambassadors/champions/super users. They'll be really important as you want to transition from old ways of working, not just change a product.
* When it comes to Windows 10, remember to not just change the OS and keep everything else around. Consider Autopilot and to manage your devices through Intune.
* Do it right from the beginning! The licenses you choose makes all the difference in the world! Consider Microsoft 365 licenses and remember to not just look for one kind (some users might be fine with F1 licenses, others should have the E5). And please don't forget about EM+S! Considering MFA? You will want to have CA for that which comes with EM+S.