Talks about thinking deeper about our goals than just metrics.

Unless there’s something that is not known about the property which would justify a deeper look.

It would be hard to remove the emotional tie from that investment with me and my family living there.

Sorry to say but business trumps emotions.

Top two things to do are to:educate yourself on the different aspects of RE, figure out what makes the most sense for your life goals, and to pursue a deeper knowledge of that areafigure out your financial situation because that will dictate what you can/can't doI guess that was more than two things...

If you want to dig deeper into the matter, here are the NC Landlord and Tenant General Statutes.

Hi Oliver, from the surface it looks like it is worth a deeper look.Where around Jackson Park is it?

Drive towards a solution where you and the tenant come to an agreement and try to remember that he's human...driven by emotional reason. 

Now that I am thinking of buying an investment property for cash flow, I feel I need a much deeper understanding of the domain.

Because the service animal is not actually living with the person who it is intended for, I was making my comments under the assumption this was more likely a "emotional support animal."