Preheat oven to 400 degrees. Prepare a baking sheet with foil. Place a colander in the sink. Thoroughly rinse produce and pat dry. Peel and slice potatoes into very thin 1/8" rounds. Cover with lightly salted water in a medium pot and bring to a boil. Cook until slightly pliable, about 8-10 minutes. Drain cherries and reserve juice. Mince chives. Rinse ham and pat dry.

Drain softened potatoes and return to pot. Add evaporated milk, 1/4 cup water, half the cheese, half the chives, and 1 tsp. salt to pot and cook until over medium heat until bubbling, about 2 minutes. Transfer potatoes to a small casserole dish, top with remaining cheese, and cover with foil (position foil shiny-side down and lightly coat with cooking spray to prevent cheese from sticking). Bake for 15 minutes. Uncover and bake until cheese is browned, about 8-10 minutes.

Heat a medium pan over medium-high heat. Score one side of the ham by slicing shallow lines in a cross-hatch pattern (This allows glaze to penetrate the meat. Plus, it looks cool.). Add butter and ham (scored-side down) to pan and sear for 1 minute on each side, or until browned. Transfer to plate and set aside.

Return pan to medium heat and add pineapple juice, cherry jam, cherry juice, 3/4 cup water, and allspice to pan. Return ham and any accumulated juices to pan and cook 4-6 minutes, scored side up, until ham has reached a minimum internal temperature of 140 degrees and sauce has reduced to a glaze. Glaze should be thick enough to stick to ham - be careful not to over reduce. If glaze gets too sticky, add 1 Tbsp. of water to loosen.

Toss broccoli in a bowl with 1 tsp. olive oil and a pinch of salt. When you uncover potatoes (7-10 minutes left to cook), place broccoli on same baking sheet. They should finish at the same time, but if you like your broccoli extra-crispy you can remove the potatoes first and give the broccoli a few more minutes, keeping a close eye so it doesn't burn.

Scoop a portion of potatoes onto a plate. Place roasted broccoli next to potatoes. Spoon glaze onto the plate. Place a ham steak over the glaze and top with a pineapple ring. Place a maraschino cherry in the middle of the ring. Garnish with remaining chives.