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I would never do a time share but maybe I listened to one too many Dave Ramsey episodes on it… I’d def opt for yearly airBnB or hotels as it gives flexibility, and allows for budget adjustments as things change
My parents and siblings (+kids and spouses) get together at least twice a year. There are currently 15-16 of us depending if we are with my dad and stepmother or my mother. I'd suggest airbnb/vrbo/hotels over a timeshare. It gives you better flexibility to plan around ppls schedules. With 7 grandkids in various stages of life (toddler to college) and going to different schools, the only school vacation overlap is usually around Christmas, Thanksgiving, or summer. I imagine with a timeshare it may be harder to schedule for those peak travel times. Doing hotels/airbnb will also give you more flexibility on where to travel and what you can do on your trips.
My parents live their time share, World Mark the Club. It's nice because the have locations all over the US and a sister company with locations all over the world. Most locations have nice condos with full kitchens, but some of the urban locations are just a hotel. https://worldmark.wyndhamdestinations.com/