Rent woes AKA My landlord makes paying the rent as difficult as possible

Let me preface what is going to become a rant by saying that I am NOT a deadbeat renter.  I have been renting since I was 18 and have lived in at least 10 different rental properties owned by at least 10 different landlords before the place I am renting now.  Each landlord has had their own rent paying policies and I have ALWAYS paid rent, on time, according to those policies.  OK preface over…

My current landlord has the most ridiculous rent paying policy ever: the rent must be in our mailbox at 9 a.m. on the 1^st for him to personally pick up.  We can’t mail it in advance or drop it off to him.  There is no grace period.  We can’t use e-pay, paypal, or any other 21^st century form of payment.  We must write out a check and, on the morning of the first day of every month, put our check into our mailbox by 9 am. Period.  No exceptions.  

I realize this sounds like the easiest thing to do but for a multitude of reasons it is not working for us.  In the year that we have lived at the apartment, S and I have forgotten to get the rent in the box at least 4 or 5 times.  Why, you ask.  Because the morning of the 1^st is an extremely small window of time when you’ve got two people who are rushing to feed and walk all the pets, prepare lunches and be out the door, half asleep, by 7:30.  Or, for instance, the 1^st falls on New Year’s Day and you are still SLEEPING when your landlord comes banging on the door for the rent at 9 am.  And, yes, sometimes we put it in the mailbox the night before but if it rains or snows we can’t because whatever is in the mailbox gets soaked (which is something that Mr. Landlord really needs to fix).  

After the last missed pick-up I was able to convince Mr. Landlord that we should be permitted to mail him the check in advance.  So this past month I wrote out the check and popped it in the mail several days in advance so it would have plenty of time to get from one side of our small town to the other.  So easy.  Except the check didn’t get delivered on the 1^st which means I got an urgent text, e-mail , AND phone message from him stating that I need to bring him a replacement check right away.  I was in New York visiting with my middle sister so I couldn’t get him a new check and the rent money was in my account so S couldn’t write him a check either to cover the missing $1700 either. 

I called him and was able to talk him off the ledge (he’s really high strung) and I haven’t heard from him today so I’m assuming the check finally arrived.  The whole situation is absurd and is really getting under my skin.  I’ve never had trouble paying my bills before and am really frustrated with my landlord for his policy and with myself and S for not getting this bill paid the correct way every month.  Unfortunately, we signed another year’s lease agreement a few months ago so we’re stuck dealing with it.  For now I’ll be adding alarms to my smartphone calendar and sticky notes around my house.  Hope that takes care of the problem because I really can’t deal with another freak out from Mr. Landlord.