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Trying to get my container bundled up (attached pic)
Can I put bags of leaves on the top? Don’t want this to block the rain water from getting in
How much to water over the winter?

You might want to have provision for covering the plant itself to prevent leaves from being desiccated in cold wind. It would not have to be covered all the time, but since it is so small, I'd cover greens for wind events. Also make sure planter can drain.