Place the squash and cranberries in the basket of a steamer pan. Add water to the pan, cover and steam for 7 – 10 minutes. The squash should be tender and the cranberries slightly plumped. Set aside.
In a large skillet, heat the olive oil. Season the pork slices with onion herb mixture and dredge lightly in the flour. Add the slices to the skillet and cook, turning once until browned on both sides. This should take about 5 minutes. Place pork in a low oven to stay warm.
Add the broth to the pan. Scrape up any brown bits and cook over medium heat until reduced by half. Set aside.
In a medium fry pan, melt the butter. Add the apple and onion pieces, pepper flakes, and sugar. Toss to coat everything and let it cook for 4-5 minutes. The apples and onions should begin to soften.
Add the squash and cranberries to the pan. Toss to coat and cook for a minute or two. Add the reduced chicken broth and any yummy bits stirring to combine. Let this cook for another minute.
Add the pork slices and any accumulated juices and let everything get happy together for several more minutes.