How much is the monthly assessment? Is this a cash flow issue or a PITA documentation issue?

I’m assuming PITA. If cash flow will board agree to special assessment to close the gap?

Are you using any management software to track accounts? If so isn’t it just a matter of entering 8 data pieces on given day after entering the mail?

Levying late fees should be automated and just a matter of post stamp isn’t before required date.