It was also somewhat of an awkward situation talking to these people who had just been through an emotional life event of losing someone they loved.

I am thinking though (I don't know if its a New York thing) but if I call somebody and I am like "Hi I am Isaac, I want to ask you a little bit about the area, hows the community, etc etc" Isn't it a little awkward, the person is going to be like "F You, who the hell are you calling me asking about the area??!?"

This is an awkward question for people who are not investors because most don't realize that its public knowledge anyway.

However, the family needs to fully understand what they are getting themselves into so as to avoid awkward holidays. 

That's awkward!  

In my state having them sign something might help legally, though it would be awkward to the relationship and impractical because I'm often doing the work when they are not around.

After the awkward budget conversation, we walked out of the house to say our good byes and the owner of the nicely done similar home walks across the street to speak with us.

@Christopher Gilly , my business partner focuses on the Florida market and yes, we have people there.

Then simply work on delivering your idea by delivering your idea over and over.It will feel awkward at first.

Can’t be in a really awkward space or create a really bad flow.