Your post interested me, but I am not sure what kind of interaction you are looking for here.

If you do get negative feelings of rejection, it's because you are anticipating and hoping for/tied to a particular outcome. 

Interacting face to face will help tremendously with forming those critical relationships to aid your progress.

Those logistics will have an impact on what types of things you can do to increase the interaction and engagement.

So buy for 100k, but in 100k, and have it worth 300k, - now it's worth all the stress, energy, time, and money this will require... you're anticipated margin is too small to make this a good deal - unless the area is so hot you see the value appreciating significantly in all the next few years. 

I know it is not far from JFK and believe the home will sell to what you anticipated. 6 months of holding seems to be plausible.

I'm anticipating a steady year with some price jumps in April-July in my market but not major. 

Interacting face to face will help tremendously with forming those critical relationships to aid your progress.

Then start the negotiations at about $150k (maybe even less if their initial price was lower than anticipated.)

I posed as a buyer at an open house in my flip and came across an interesting problem I did not anticipate.