I have the garmin forerunner 305 and I have plans to upgrade. I have even bought a spare battery just in case the current battery dies off.
Though I use it mostly for running just to get an idea of the distance, my most desperate need comes when I need to load a course. I did load a course when I did the Kotai 200K express. I followed some instruction and garmin connect website had classic mode enabled that time. It was not difficult.
Lately, without the classic mode, I just couldn't find a way to do it. The modern UI does not have anything yet under the training section, which is what garmin 305 uses for map course. I also did load a route (not just 100 waypoints, but many more). I cannot figure that out as well.
You might think, the obvious other option would be to upload a .tcx or .gpx file as activity and then convert the activity to course. But connect.garmin just fails to process the courses (.tcx) and gpx tracks. They fail with some error unless the tcx was directly from a garmin log itself. So, it is of no use unless garmin fix these issues.
Cut short... what is the way now?
This is what I followed.

- Convert to a .tcx (from various formats) using http://www.gpsies.com/convert.do
- Download garmin training center from http://garmin-training-center.soft32.com/free-download/ or directly from http://files.freetrialdownload.com/40/393280/845049/TrainingCenter_365.exe. If you go to garmin site and click at the training center link http://www8.garmin.com/products/trainingcenter/ you will be disappointed, because that link redirects to mapsource which is almost like training center, can do many things like route creation, etc. But has the same issue of being enable to send course to device. So, use the earlier link.
- I also had trouble in detecting garmin device in spite of having windows 7 with all latest patches. Then I had to install garmin USB driver : http://www8.garmin.com/support/download_details.jsp?id=591 With that, the device was detected irrespective of whether it is on or off. You might have to try similar ant driver for other devices that don't have USB port for charging, such as 310XT.
- Once in training center, you can receive activities, tracks, courses, etc. from device and convert any activity log into course. Or import from user account -> courses... to open and import the .tcx file created using step 1.
- This will create a folder under the Imported Courses. Please note that the .tcx file could be activities log. If you open the tcx file and look for activities keyword. If it is found, it is an activity log. If you find courses keyword, it is a course. You need to choose the import type correctly.
- Using toolbar, send to device. Wait till the device says transfer complete. Then go to training, courses and you will find the course.
- Make sure that the device settings -> General -> Map has Show Map as Yes, User Location as Show and orientation as Track up so that you will get to know your direction of movement and thus can anticipate and decide turns accurately.
Note that older devices like mine accepts about 13K trackpoints in the course. Newer devices like 310xt accepts more than 40K trackpoints (from what I have tried) and it can thus accommodate a course as far as 10,000 km if the roads are normal, not too much unpredictable turns every 10 meters.
Enjoy navigating through your watches :)