The hand delivery was to soften the blow.I welcome each to resign on a month to month lease, at the new rate, and plan to update each unit as they vacate and raise the rent again.

Purchase a ball-gag from Amazon along with 50 Shades of Grey, and leave them on her doorstep as a present.  

sect...It's Section 1962(f):(f) If the address provided by the owner does not allow forpersonal delivery, then it shall be conclusively presumed that uponthe mailing of any rent or notice to the owner by the tenant to thename and address provided, the notice or rent is deemed receivable bythe owner on the date posted, if the tenant can show proof ofmailing to the name and address provided by the owner.

Be aware if your jurisdiction has “1 business day” delivery times or similar for digital service you may need to adjust scheduled dates

Put that in writing, and mail it to him with delivery confirmation, and you could always email it, too.  

There is no requirement that I be at the beck and call of the mail delivery and then forced to rush to the bank so that my tenant can pay via check.

If you knew about it, and are sure you owe it, you should pay it with proof of payment/delivery.

It's all about word-choice and delivery.

The new tenant paid me monthly installments on that oil bill until it was paid off and ran low enough for them to start calling for deliveries on their own.

Maybe leave a bottle of it on their doorstep with a bow on it.