Don’t know if this might be the issue but assuming the reservation and the credit card are in the same name. We changed from the free cc to the fee card and I started to book something in one name while the cc was in the other and it wouldn’t allow me to do so. I finally reached a CSR and she told me to cancel the reservation and start from square one. Once everything was in the same name there was no problem and we each got a free checked bag.

Re your first question, I’m thinking once you’ve checked your bags you can go directly to TSA and then to your gate but I often get the steps confused.

Have an awesome trip! 🤭🤭