Late rent issues

I have a residential rental property here in Orlando.My tenant of 26 months
has always paid on or before the 1st of every month.However this month they
have asked for an extension through the 14th of the month.The lease states
rent must me paid on or before the 5th day of each month . I am confidant
they will pay however I realize this could become sticky.Is it possible by
allowing them to pay late I am jeopardizing the terms of my lease or for
future reference recasting or redefining the terms of this lease.How can I
work with my Tenant and not jeopardize myself ?? Could this make it more difficult for me to evict them if necessary in the future ??

Good question. The easy way to do this is to send them a notice which restates the lease policy on late payments. Then state in the letter that you are willing to allow a late payment by xx/xx date (with any late fees listed in your lease) on this occasion only. Further state that this will not set a precedent and that this late payment is permitted for only this one time.

This prevents it from looking like a precedent. And you still will be able to evict should they not pay you by the date stated.

I faced the same issue.

Thanks for the advice!