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Are you still living in the building?
How did you pay the rent for May to August, did you mail it in or deliver it personally?
Ok, if you have paid all the rent that you owe each month on time but the landlord hasn't cashed the checks then that is his issue to deal with.
You would have proof through your bank records showing the uncashed check number each month to prove that you did write a check to the landlord.
Why he isn't cashing the checks I can't say but you need to make sure that the money is in the account to cover them all should he try and cash them all at once.
But a judge is not going to consider it harassment if he just isn't cashing the checks....