I got a brand new Edge 500 yesterday and went for my first ride today. Being very experienced with the Forerunner 305 I was looking forward to using this bike-centric upgrade.
I had a lot of trouble getting my files uploaded though. I normally use SportTracks but it doesn't seem to have support for the Edge 500 (as of 3/17/10.) So I tried GTC (Garmin Training Center.) Out of habit, I used the self-update check to see if there was a later version of GTC. It found a later version and installed itself. I was to find a problem with this later though.
First, I forgot I had to add the Edge 500 as another device so it took about an hour on/off to get to that point.
After you add it to your device profile you'll see this:
The next obstacle was that GTC failed to see the device. I tried using different USB ports, etc. I even connected my 305 and it popped up just fine. So after typing "Garmin Edge 500 - Problem communicating with device" into Google I found a post indicating that the GTC version might be the culprit.
Since I had already done the version upgrade I didn't think this was my issue. But I checked the version I had running anyway (Help, About) and to my surprise it was version 3.4.3. I know that I downloaded version 3.5.3 earlier.
Long story short, the software upgrade did not uninstall the previous version. I had to manually go to the program (program files, garmin, etc.) and created a desktop shortcut for the new version. After double-clicking that shortcut, I checked the version and got this:
Surprise surprise, my Edge 500 was found and my files were uploaded. Now I can get back to work on my training.