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Place beets, vinegar and rosemary in a single layer in a large saucepan. Add water to cover by 2 inches. Bring to a boil, then reduce heat to maintain a simmer. Cover and cook until the beets are very tender, 1 to 1 ½ hours.
Meanwhile, whisk goat cheese and milk in a small bowl until smooth. Stir in chives and a pinch each of salt and pepper. Set aside at room temperature.
When the beets are cooked, transfer them to a cutting board. Cut each beet in half horizontally. Lightly press on each beet with a sturdy salad-size plate or mason jar to flatten it, but keep it intact. Sprinkle the remaining ¼ teaspoon salt and pepper on both sides of the beets.
Heat 1 tablespoon oil in a large skillet over medium-high heat. Add half the beets and cook, turning once, until browned on both sides and crispy on the edges, 3 to 6 minutes total. Transfer to a plate.
Add the remaining 1 tablespoon oil to the pan and repeat with the remaining beets. Serve with a dollop of the goat cheese mixture.