Program vs. individual workout?

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Very interested in this site / service and enjoyed the one workout I tried out. I'm on a mission to get some healthy habits going (I'm a mom in my early-forties) - curious about the benefits of a "program" vs. just choosing workouts at random on the site.

I'm looking at the Bodyweight workout and the 30 day trial. I do Pilates and run irregularly, so I'm reasonably fit, but not in a great daily workout habit yet.

Welcome any and all advice!