Heat a medium pot over medium heat. Coat the bottom of pan with a good amount of olive oil. Add the apples, onion, fennel, fennel seed, salt, and black pepper. Saute until the apples have softened and all of the vegetables are tender.
Meanwhile, preheat the oven to 350°F. Heat a large pan over medium-high heat and coat the bottom with olive oil. Season the pork loin with a generous amount of salt and pepper. Sear the pork loins on all sides until each is golden brown. Transfer the sautéed apples and fennel to a baking dish and add the chicken broth. Place the pork loins on top and pour the drippings from the pan into the dish. Bake uncovered for 30 minutes. Cover with aluminum foil. Finish cooking until the pork is cooked all the way through, about 10 more minutes.
Let the pork rest for 10 minutes before cutting it. Meanwhile, blend half of the apples and fennel (along with all of the liquid in the baking dish) until smooth. Reserve the rest as is.
Add the Parmesan to a large bowl. Cut the pork into medallion-size pieces. Toss each piece of pork in the Parmesan, rolling it and packing the cheese into the meat. Either serve it immediately or broil the pork on high for just a minute so the cheese forms a golden crust.
Spoon the apple & fennel puree onto a plate. Top with the reserved roasted apples and fennel. Place the pork onto the puree and garnish with fennel fronds.