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That said, she has never tried to stop me from doing it, she just has never expressed any interest and generally tries to avoid any conversations dealing with the subject.  

Is there a book or article anyone can point me to as far as the conversation one has with perspective owners to determine investment opportunity?

@Jimmy Calabrese I am assuming this is in reference to "in person" conversation or phone conversation and not email.  

Thank you all for the great conversations in 2016 and I look forward to a great 2017!

I recently had a conversation similar to this one with my realtor.

The reason is because the home had a garage conversion a long time ago.

If it's zoned as a SFH and only has one APN lookup your local laws on 'Accessory Dwelling Units' it's entirely possible the conversion was unpermitted and you'll get in trouble/have to rip out the 2nd unit if any code inspector finds out about it. 

In these types of conversations you will learn what to look for.  

Usually it's a garage conversion, so you lose the appeal of a garage.