Hi Alan,
Sorry for the delay, I didn't get an email with your reply and just spotted it on the group.
The possible start times are on all 1, 2, 5, 15, 30 minute boundaries so I imagine to do them all at once
you would have to save overlapping audio files to send off to WSJT-X at the appropriate times.
Sounds a bit messy and don't know if it would fit with how you do the decodes.
73, Neil G4BRK