For the voice keyer are separate configuration provided; one for your ‚normal‘ logging, one for contest operation. See the appropriate Preferences under the Phone tab. The Auto CQ option is available in the contest only. RUMlog can switch the PTT, see the TX 1 settings.
The audio file to play must be located in the folder: ˜/Library/Containers/de.dl2rum.RUMlogNG/Data/Documents/Voicekeyer_Recordings and can be easily selected using the popup menus. You can choose different output devices for play back over the radio and for play back just to test the file.
Use the F1-F8 function keys to start the play back. The appropriate menu items can be found in the CW menu.
For the IC-7300 the audio source can be toggled automatically, see *Preferences–>TRX–>Transceiver Specific–>Settings