Hello Julie and thanks for bringing such a great question to the Disney Parks Moms Panel.
Like you, many Guests look forward to participating in a lively and fun performance from
Yehaa Bob Jackson at River Roost Lounge during their jolly holidays at Walt Disney World Resort; he's such a popular guy!
One of my personal favourite entertainments at a Disney Resort is
The Grand Floridian Lobby Society Orchestra; just sitting back and listening to the wonderful jazz inspired tunes is practically perfect in every way for me!
However, as an alternative type of entertainment to enjoy especially with your little Mouseketeer you may like to consider
Chip 'N' Dale's Campfire Sing-A-Long at Disney's Fort Wilderness Resort; all the marshmallowy fun is then followed by a classic Disney movie under-the-stars.
Another great laid-back spot to visit during the evening hours is
Disney's BoardWalk where you might be lucky enough to catch some wonderful street performers entertaining passers-by.
I'm sure what ever is finally decided upon you'll enjoy a magical visit to Disney's Port Orleans Resort ~ Riverside making memories with your dear family which are sure to last an entire lifetime.
Have a great Disney day.
~ Jane