I followed the trusted and popular method of just calling again and trying a different agent. This worked and the issue got resolved. Only took a few phone calls. They are booked in comfort plus now on the return flight.

I also linked all the tickets together so hopefully we can check in together and they get a free checked bag for my medallion and / or delta amex.

Good grief. Only impact is I moved 100k MR points into Delta in case I had to cancel and book fresh. Those miles are now committed to delta but probably where I would use them anyways.