I already set up garmin express once, and used it a couple times to sync my data. Today when I started it up, it wants me to start all over again with the "first step". Apparently it has lost my data. Losing data is a showstopper.
Sorry you are having these problems, once Garmin Express is installed to your Mac you shouldn't have to re-install it or start over. I would suggest following the steps in the FAQ: How do I install Garmin Express on the computer? If you still have problems call the customer service 800-800-1020 number for additional help.
Chris, I saw exactly the same behaviour today. I ended up rebooting my Mac and then Express decided to re-install itself without any involvement from me. It then picked up the existing configuration. Very strange.