If you are a RE agent spending that much money on marketing every month, what are the demands to exceed that expenditure?

That is how I liked it.The only thing I approved was expenditures over 300 dollars.

@Ryan Guffey Use stessa.com app (free not sure for how long as it's recently acquired by RoofStock) It can pull transactions from bank, convert receipt sent from email transactions, and many cool reporting feature such as income, cash flow, capital expenditure.

The bigger issue you might find yourself in is potential evictions and the expenditures that go along with it.

And the captial expenditures I would have saved by that time would not be sufficient enough to replace them. 

I don’t like keeping properties past 5-7 years because the capital expenditures tend to become very costly over time like @Steve Vaughan mentioned.I also like what @Sam Shueh mentioned about the note buying.

You're $9.00 upside down each and every month outside of expenditures.

Ex. expenditures and mildly reduce your Mts. expenditures so you should still be in good shape. 

Of course, I also account for capital expenditures, future vacancies, future property management, etc, but so far, it’s working out pretty well!     

While you may never fully break the bad habits, you can at least rest assured that you're providing a safe place for your elderly tenant and (hopefully) minimizing the waste of your time and expenditures.