This has a doubly negative effect – shorting your own potential income, and perhaps crushing a struggling tenant with that recurring fee that “breaks the camel’s back”.

The tenant is in control of starting the payment and they can set up recurring payments and reminders, but I have no control if they do this.As landlord, I find out from WilliamPaid by email when a payment was initiated, but it takes about 3-4 business days to appear on my checking account.

I created an excel template of recurring monthly transactions (i.e. rents, garbage, pest control, landscaping, etc.), I key the PM transactions into it and then import it into Xero.

For routine maintenance to be immediately deductible, the IRS wants the expense to satisfy all four of the following criteria: Repairs are regularly recurring activities of the type you would expect to perform;The repairs result from the wear and tear of being used in a trade or business;The repairs are needed to keep the property operating efficiently in its normal condition;And it's fully expected that the repairs would need to be performed either: More than once during a 10-year period (for buildings and structures related to buildings), orMore than once during the property's class life (for property other than buildings).

Pretty sure there are email reminders, but they can also schedule recurring payments so they don't need to "remember".

I would like to have document references to support classifying these two expenses as Maintenance (not repairs) so that I am safely classifying these costs under the Safe Harbor for Routine Maintenance.Also, it is my understanding that the Safe Harbor rule for Routine Maintenance stands apart form the Safe Harbor Election for Small Taxpayers which is an issue due to the 2% rule.Safe Harbor Election for Small TaxpayersThe total amount paid during the taxable year for repairs, maintenance, improvements, or similar activities performed on such building property doesn't exceed the lesser of- Two percent of the unadjusted basis of the eligible building property; or$10,000 (for questions about how to calculate the unadjusted basis, refer to "Figuring the Unadjusted Basis of Your Property" in Publication 946Safe Harbor for Routine MaintenanceYou are not required to capitalize as an improvement, and therefore may deduct, amounts that meet all of the following criteria:Amounts paid for recurring activities that you expect to perform;As a result of your use of the property in your trade or business;To keep the property in its ordinarily efficient operating condition; andYou reasonably expect, at the time the property is placed in service, to perform the activities: For building structures and building systems, more than once during the 10-year period beginning when placed in service, orFor property other than buildings, more than once during the class life of the unit of property.Thanks in advance for any guidance you can provide.

Typically on your rental application you would ask about all recurring obligations.

Your landlord won’t fix a recurring problem and you’re still paying rent.  

If the pest control becomes a recurring problem you need to screen for tenants differently.I'm not sure about 'bama but in FL any of the 30-50K homes I buy the taxes are about $5-700/yr.

Would recommend a recurring campaign (minimum of 2-3 mailers over 5-6 months).- Facebook geographic campaign using a Lead Ad,  Would recommend this on during mail drop and for a few weeks before and after.