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If it was directed to me I don't think you read it in the context of the conversation since it was in response to his last question.

In casual conversation, you most likely can ask about - where you went to school, what are your hobbies, etc. 

He records other tenants conversations, calls police on them three times for something stupid.

I just don't like the tone of the conversation, which implies that I'd better figure out a way to get this done, or else.  

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Many times former primary residences don't make the best rental conversions. 

If anything, they dont take your offer or even better, they counter offer.Start the conversation and get the ball rolling!

The virtual showings aren't ideal as they have a lower conversion rate, but it's really the only way to get people to actually inquire about it because in-person showings have dropped considerably. 

While showing him the apartment and engaging in conversation, he revealed to me that he has 6 children that live with his fiancé and that DCS won’t allow him to live with the children because he has blackouts due to PTSD.