Can I schedule overlapping trainings?
Yes, but organizers can't host them both at the same time. It is possible to schedule more than one training for the same time slot, but you can only host one training at a time. You will see a message warning you about the conflict when you attempt to schedule trainings that overlap, and you also will not be able to launch a new training until you end your last one. However, if you're already in a training and need to leave without ending it for everyone, you can promote any attendee in that training to be organizer so the session can continue on without you while you switch to the next one.
If your organization needs to host multiple sessions at the same time, then you can upgrade your plan to add additional organizer seats (these individuals would each get their own account with which they can schedule and host their own trainings).