This is one of the most unfortunate things as a lot of Mom-and-Pop investors get very invested emotionally in long term tenants and don't feel it is "fair".

Sales is emotional, and you need to create excitement without creating unrealistic expectations.

Fear is a very powerful emotion that wears many different masks and often leads to aggressive, sometimes irrational and anti-social behavior.You mentioned empathy and said...- "What if I knocked on your door during dinner or showed up to your work in the middle of the day in order to sell you something?

So this is not a financial decision as much as an emotional one.

So my only recommendation would be to make what you are living in be a non-emotional decisoin and plan on making that a rental.

I found it easier to deal with the job I was emotionally done with when I knew I was building my exit strategy.

Also, be ready for those who say their pet is a service animal or emotional support animal.

When you are dealing with someone like this it's hard not to get your emotions in the way but that's exactly what you have to do to. 

The best investors I know would tell you they do not need a cheer leading section or an emotional support team. 

One of my favorite simple hacks for dealing with difficult guests is to use conversational AI to respond to a nasty review without being emotional.