With the slowness of today's post office, I would recommend mailing anything two weeks ahead of time when you want it delivered.
There are those that consider a debt paid on time if it is postmarked by the due date. Others require that the payment is
received by the due date.
My previous Association was in VA. We considered it late if
not received by mm/dd/yyyy. We stated that clearly in a resolution and on our invoices/payment books.
Being "received by" seems to be the norm.
That said,
VA § 55.1-1824, applicable to HOAs,
defers to the governing documents. However,
if the governing documents are silent - then late fees apply 60 days after the due date.
Again - I would allow 2 weeks for a payment to go through the mail system.
As far as informing the owners of the assessment, we give 30 days notice (annual assessment notice/coupon book mailed just after thanksgiving).
I found nothing specific to notice of assessments in the VPOAA, but it appears that 10 business days (2 weeks) is considered reasonable.
Note: some references identify 5 business days after being mailed is considered delivered.