You can't become emotional about real estate.

Crazy as it seems, sellers in emotional distress and denial over whizzing away their parent's legacy would much rather whiz it away to a local agent who is deeply embedded in their community, who works the soft-serve at church festivals and reads off the bingo numbers at the VFW hall and brings some of his homemade kielbasi to the volunteer firemen's BBQ benefit.Do not discount your local agents who have been eating rubber chicken to pass the card at Rotary events for the last twenty years.

It is good that you have emotions but learn how to control them. 

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.

Anyone who wants to move in will just get a letter from a doctor stating that their animal is an Emotional Support Animal and there is nothing you can do about it.Increase the rent, increase the security deposit, and advertise pets are OK.

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.