As you know, October 13 2020 is approaching fast and the support for Exchange 2010 is ending.
For those who are still on legacy, remember Windows 2008 R2 is not getting many or any updates anymore so you at a risk with that operating system.
If you want to move to Exchange 2019 you will need to do that in a double hop. Currently you can only migrate to Exchange 2016 as the highest on-premise coexistence environment with Exchange 2010.
Start your planning for whichever direction you are migrating, if it’s Office 365 then get your Hybrid Server in place, configured and tested.
If you are moving to Exchange 2016, start your planning with the number of servers needed, sort out your licensing and get the VM’s built and coexistence started. JetStress your storage to ensure it can run everything without an issue. Get your testing complete so your migrations can start as soon as possible and you can decommission Exchange 2010.
Happy Upgrading.