This investor is VERY thorough and analytical so I know the liability reasons alone will not be enough to satiate his demands.

Hello all, I'm working with a motivated seller and I'm going to approach them with a sub-2 offer. 

Nothing wrong with the Kiyosaki approach; "because your home is a liability", so cash out and preserve your equity by moving proceeds into other assets. 

How should i approach people that are expecting market value for their property?

I really think you could benefit by taking the same approach as me.  

The "owner" said she had done a loan modification which she did not make any payments for so I'm wondering if she didn't give up the "normal/public trustee process" approach in exchange for the loan mod.

--Is there a support-approach the founders/managers just modeled so well, everyone else just followed?

Approach the subject of real estate investing as a person and not as a woman.

You appear to have a few well thoughtout approaches to go with.

So it may be better, for the good of your reputation and potential long term relationship with this agent, to approach them with that in mind.