That isn't to say you can't increase the rent because he's been there for 2 years just do not mention the emotional support dog.Tell him you are moving out and want both units under an annual lease. 

Having a house broken into is so emotionally trying.

I'm sure he's a nice guy and all that, but you're asking him to suffer - mentally, emotionally and financially.....not to mention the other tenants and residents of the premises and area.

Even with an emotional support animal. 

“Businesslike” investing suggests a less emotional, better organized, well thought out approach to real estate.

Try to remove your emotional connection to it. 

However, I recognize that there is definitely a high degree of emotion behind that and it may not be totally financially sound.I am primarily thinking about that one house that survived in Mexico Beach and applying some of their principles to construction and upgrades in order to mitigate potential damage and give my tenants as much peace of mind as I can. 

No emotion. 

The day I put my first multi-unit property in escrow I make a promise to myself that I would never let a tenant get me emotionally upset.

Their business decisions are governed not by common scense but rather by emotions.