It was totally dated and most of the rooms were ate up by termites.

I ended up with a much nicer house almost completely remodeled but had to suffer through a 3 month vacancy period that ate up all my reserves at the time.

She seemed to be a pretty hands-on landlord, she even visited and ate dinner with some of her tenants haha.

Nor did I realize termites ATE UP an entire section of sub-floor where some of Seller's personal possession had been piles. 

I had looked into it before but in every scenario I encountered the caregiver expense ate up the majority of my profits.

They could have been uneducated about other options or maybe the loan officer they refer those loans to ate all of their Oreos that were in the break room while they were on vacation!!

And by the way, that $100 / month didn't cover the backed-up sewer drain, the toy that was thrown in the toilet that you had to argue for 45 minutes why the tenant had to pay for that and eventually just ate the bill, the broken storm door that the "wind" ripped off the house... 

I have a little experience with flipping properties in the past but one bad investment decisions ate through any previous profits.

Experienced investors will have ate that all day long, and accepted a smaller margin in this market. 

I'm not saying I know the lifespan of all of these bigger item expenses to a tee or that I can forecast everything that will happen (I am just a little newbie), but my idea behind the way I am budgeting for these bigger expenses is that they should be mostly covered in the long term, given their life expectancies.