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You can scare them though. Some boards don't like lawsuits. Because then the residents find out the board's secrets. And a manager's secrets are allowed by the board so, either way, the board's found out.
People who do clerical work are often non-thinking and/or not too bright.
I was assigned to the student loan department when I worked for the State of Illinois. We received millions of checks and had to input them at a certain rate. Letters and all non-check contents went into a bin to get shredded. They weren't even read. This is usually why there is a different mailing address/PO Box for correspondence and payments for larger companies/organizations.
I would assume your HOA is not dealing with that volume of checks, though, so they probably should take the time to review all contents and do the research necessary to apply the payments appropriately.
This would tick me off. I think if you went to a HOA meeting and brought it up (after getting some support from some neighbors) they would be embarrassed enough to waive the late fees.
Go with all your supporting paperwork and with a "friendly" attitude, ie. not loaded for bear. Especially since you are new to their system and if you say in the future you will put both account numbers on the checks or send separate checks they should act like human beings.
At my HOA, we had a similar situation as the OP last year. When the facts were made clear at the monthly BOD meeting, the late pmt fees were waived by the board in full. I feel that the OP clearly did nothing wrong.
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