In almost every instance the reason to stuff one food with another is appearance. So for me the questions are: Is it easy enough to make it worth the effort? Does the process add or detract from the overall flavor?
I've gotten to the point where I no longer feel ravioli are worth my time, for example. I love the way they look, but they taste pretty much the same as fresh pasta with sauce. I haven't stuffed a turkey in 20 years because it's counterproductive: the stuffing gets worse when you cook it inside the turkey.
I do like stuffing chicken breasts with greens, though. The chicken juices seem to contribute to the greens' flavor, even if subtly. But the whole pounding and rolling process became burdensome. Call me lazy; I am.
Here is a technique that has it all. It's easy, it makes chicken breasts taste good (no mean feat) and, as an added bonus, it produces lots of servings without much effort.
Take two chicken breast halves and pound them just a little. If they're an inch thick at first, maybe take them down to three-quarters of an inch. Lay some cooked greens on one, put the other on top, and tie them together. It's really not stuffing, but layering.
The cooking of greens and chicken takes place in one pan, first on the stove top, then in the oven. The resulting dish not only looks impressive but tastes better than chicken and greens served separately.