I own in Tampa, Florida so housing hacking there has been a reoccurring theme.

For example if you are going to purchased something like (some) pest control companies or an alarm monitoring company where the income is contractual and reoccurring you will generally pay a higher multiple, say 5 times NOI. 

The thing is how to stop it from re-occurring?

Look at mechanical, roofs, appliances etc. to reduce potential for reoccuring repair & maintenance issues and making move-in ready.If you provide a decent analysis of the property which peaks his interest, and he buys and finds you were spot on, whose properties is he gonna look at in the future?

Best part its a re-occurring check so now no need for reminders.

Ballpark..Property is at the bottom of a hill and water in the basement has been a reoccurring issue.

Many of which are reoccurring such as signing a new lease or a new move out etc.  

Meaning if you were sent notice and didn't remedy or if the problem became reoccurring. 

We took the hit & replaced it all, because it was the proverbial re-occuring nightmare.But I also put in a backflow valve to prevent the likelihood of neighborhood sewerage flooding back during heavy rains.

This is something that Buildium, Appfolio, or Yardi offers at a reoccurring cost.