yes, if you can access the data on the Macs internal drive you would need to copy ALL the music from old to new drive and try and keep the location the same and also you need the info in the Pioneer folder
once you boot up the new drive, name the computer the exact name so the path stays the same for waveform and cue data, this is the easiest way to make sure it all comes over right
install Rb on new mac, open it so it creates the needed ~/Library/pioneer folder
go on the old drive (you need to show hidden files, google how to do on mac, easy terminal command) and look for: users/username/Library/pioneer
copy the pioneer folder and overwrite the new existing one so all the data copies over to the new drive