Hi Andrew,
Sorry for the late reply, but if it still helps, you can directly migrate your environment and update it without installing OutSystems 10.
The reason I suggested as a first option to install OutSystems 10 and later upgrade it to 11, is to make sure that if your migration cause any problem it will not be confused with the upgrade.
However if you feel confident or have a small time window... you can restore your DB with OutSystems 10 in a new server, install OutSystems 11 directly and run its configuration tool.
The only thing you should pay attention is for the migration steps.
When migrating to a new server using a DataBase clone there is a few steps you should do to clean some old data. This steps can be found here.
So summarizing. You would need to:
-Restore your DB to a new DB server
-Run the steps to clean old data
-Install OutSystems 11 in a new Windows Server
-Run configuration tool pointing to the restored DataBase
After that you will need to republish your entire factory and fix any problem with your code.
Hope it helps,
RR :)