I practice in a similar (if not the same) field in NYC, am a huge FIRE fan, and prefer to buy and hold locally though I'm willing to consider a flip under certain circumstances and possibly even out of state.   

I have a 3 year old appraisal at 275k with EIGHT units on it because the seller had a fully functional, rented detached single-wide on the property that went away between then and now (not clear on the circumstances but it rumor is it's divorce related).

This situation was very difficult for my wife and the other kids because it was their circumstances and they had no way to change it.  

Local REI women's group I hear is a must!

Later when I hired and did comp plans for salesmen/women I made sure they made as much money as they possibly could.

It is something that depends on your unique circumstances coupled with an analysis of the law where you have the properties and where you live or do business or both. 

Only in a few specific circumstances, it can be started sooner.

I guess I liken it to picking up women.

But proactively doing something for the tenant is a lot cheaper than the damage a psycho tenant would do under the circumstances.  

It does not apply universally to every individual and unique set of circumstances.