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Combine cucumber and vinegar in a bowl and refrigerate to soften and pickle (overnight, or up to 4 days).
For pita dough, combine yeast with 250ml warm water in a bowl, then add oil. Combine flour and a pinch of salt in an electric mixer fitted with the dough hook, add yeast mixture and knead, scraping down sides occasionally, until a wet, sticky dough forms (5 minutes). Cover with plastic wrap and leave in a warm spot until doubled in size (1 hour). Roll dough into golf ball-sized balls then, working with one at a time, roll out on a clean surface, dusting with flour to prevent sticking, into long oval shapes about 5mm thick. Cover with a damp cloth and leave until doubled in size (30-40 minutes).
Meanwhile, preheat oven to 120°C. Roast chilli on an oven tray until crisp (10-12 minutes). Cool, then break into flakes.
Heat a large frying pan or char-grill pan over medium heat. Cook pita in batches, turning when it begins to puff up, until golden and lightly charred (2-3 minutes each side).
Spoon labne onto a serving plate and create a well in the centre with the back of a spoon. Fill well with pickled cucumber, sprinkle with flaked chilli and drizzle with oil. Top with dill, season with salt to taste and serve with pita scattered with oregano.