How much technical expertise is required to make the maps?
Going from your GPS system to Google Earth is pretty simple. Follow instructions that came with your GPS system to write out a .gpx file. Newer systems probably can do this directly. If not, there are conversion programs on the web that can make the .gpx file from whatever your GPS system writes out. Google Earth can read the .gpx file. After that, you will use Google Earth to manage the tracks and move them within folders, etc.