We are looking for a better way to manage all of our contacts, conversations, set future tasks with the leads that dont materialize to follow up, etc.

Get the seller on the phone, and reinforce those issues in your conversation. 

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Your job is to get the prospect to call without misleading them or setting them up for unrealistic exoectations during conversion.

Depending on how that conversation goes and if you can collect timely would determine my next move.  

@Redgy Saint-Germain I suggest you have a frank conversation with him about what he's willing to do and what he isn't.

The tenant might try to use that later on for negotiations.You can have all the hard conversations you want but when the rubber meets the road if it is pay the rent, have utilities, or watch the kids eat the latter 2 take precedence to a lot of people.

Don't make it a long conversation but definitely ask what they are looking for.Best of luck!

I am also hoping my conversations has turned her into an ally.

Well, now I hope it's legal to record phone conversations in Tennessee so Account Closed, if someone was really looking for an apprentice the would just have look here on BiggerPockets.