In a microwave-safe bowl, combine vinegar, 1/3 cup water, and dried tomatoes. Heat, covered, in a microwave oven at full power (100%) until steaming, about 45 seconds. Let stand, stirring occasionally, until tomatoes are soft, about 20 minutes.
Meanwhile, in a 5- to 6-quart pan over high heat, bring about 3 quarts water to a boil. Add the penne pasta and cook until it's barely tender to bite, 10 to 12 minutes. Drain.
As pasta cooks, lay prosciutto strips on a microwave-safe plate and heat in a microwave oven at full power (100%), stirring once, just until hot, 15 to 20 seconds.
Also, pour canned tomatoes into a strainer over a large bowl, then chop the tomatoes and add to juices in bowl. Add dried tomatoes and soaking liquid, garlic, parsley, pasta, and olive oil. Mix, and add prosciutto and 1/4 cup cheese. Mix again, and add salt, pepper, and more cheese to taste.