I'm surprised they didn't say with one free checked bag and charge for second.
Years ago when food delivery was very sparse at disney, we checked 4 bags. One was food. One was kids stuff (toys, diapers , etc) , two were clothes. And we had a backpack and gym roll bag. Now with kids older, and 20 choices in food service, we have two checked bags about 35 lbs. The same backpack and roll bag and a DVC tote bag, that carries his medical needs comes onto the plane. Our checked bags look about the size of some of the carryons I see.
SW had to know with the years of free bags, lots of people would be saying why bother staying with SW.