I am having almost exactly the same problem with my Forerunner 210. It appears to start up Garmin Express, and then is successful in sending. The message comes up with "Nothing to Sync." I actually hate having to use Garmin Express. It keeps telling me that there are 3 updates to install, but I have installed them over and over. The upload of new workouts was also much simpler when using Garmin Connect "Classic" with no intervention from Garmin Express. I've had difficulties with sending the calendar to the device too. Eventually, it works, but it is wasting hours of my life! Garmin Express stinks!
I have the same problem and have to switch back to the classic mode to upload any courses. The Garmin Connect is one of the worst, most buggy user interfaces I've worked with. I've contacted their support but as the lovely disclaimer states, they don't "guarantee a response". Awesome company to work with so far.
