I have two rooms booked for December. One with my name and the other one with my DS23 name. The email confirmation is my email. Will TP send my room requests for both rooms? I have two trips set up on the dashboard, each with their own request.
Yes, I had two set up the same way and just got two notifications that ours went through a few days ago. Just make sure you have the right room reservation number with the name on the reservation for each one 
Yes, I did this in August.