I think yes. In general if you have good setup instructions (preferably automated) then it will be easier to start from scratch. This is because when starting from scratch you need to worry about the new setup. But when upgrading you need to worry about the new setup as well as any cruft that has been carried over from the previous setup. Basically starting clean has some advantages.
However it is important to make sure that you can go back to the old working state if required. Either via backups or leaving the old machine around working until the new one has been proven to be operational.
I also really like NixOS for this reason. It means that you can upgrade your system with very little cruft carrying over. Basically it behaves like a clean install every update. But it is easier to roll back if you need to.