Cut the cuttlefish in strips. In a bowl, toss the cuttlefish together with the fennel or dill fronds, ¼ cup of the olive oil, and salt. Let the cuttlefish marinate at room temperature for 20-30 minutes.
Bring the broth to a simmer over medium heat in a saucepan. Add the saffron and let it steep until the broth is a rich, golden yellow color. Keep the broth hot.
Heat the remaining oil in a large pot over low heat. Add the shallot and garlic and cook, stirring frequently, until the shallot is tender and translucent, about 4 minutes. Add the fregola and the tomatoes and stir to coat evenly with the oil.
Add enough of the broth to cover the fregola by ½ inch, and cook, stirring occasionally. As the fregola absorb the broth, keep adding more, and cook until the fregola are tender but still have a bit of bite, about 12 minutes. (They should be quite moist, with a loose but not soupy consistency.)
Add the cuttlefish and the parsley and continue to cook just until the cuttlefish is cooked, for 2 more minutes. Season with pepper, to taste. Serve at once on heated plates.