GarageBand multiple takes doesn't work

Do you want to record multiple tracks, or multiple takes?

For multiple takes you need two things

1. Make sure Cycle mode is on
2. In General settings (GarageBand/Preferences/General) Cycle on is set to Create Takes

To record multiple tracks simultaneously:

1. Make sure that the Record Enable button is shown
2. Activate recording for multiple tracks. You can only do that for separate input channels.

You shouldn't (need to) stop and rewind. On the yellow bar on top of the screen, set the region you would like to cycle. Garageband will do the rest.

With pictures:

http://support.apple.com/kb/PH1913?viewlocale=en_US&locale=en_US