Executing a reload or shutdown inside an if/else block results in the reload or restart occurring before the other commands in the batch are executed.

if (outcome == success) of /subsystem=logging/logger=org.jboss.as.cli:read-resource()
   /subsystem=logging:write-attribute(name=use-deployment-logging-config
   shutdown --restart=true
end-if

This command will actually leave the server in a reload-required state. The shutdown, or reload, will occur before the write-attribute is executed.