So I sat down and started reading @Brandon Turner 's book on creative investing and about 3 pages in, I realized I am approaching this entirely wrong.

I don't want to approach someone working on a for-sale house and ask, "So. . . is this a. . . good deal?"

Take a look around BP for the "90 day challenge" - plus I would bet on a number of upcoming resources and webinars designed to help people with buying their first property by the end of the year.If you've already done all that and are still struggling with which direction to go, the bottom line is that it doesn't matter.

Looking for: - best way to approach the situation? 

“What’s the biggest challenge you face?

You're going to approach those completely differently.

Typically for government backed loans it's more challenging to get a "very low offer" approved as they are less flexible for their NET and they use more qualified people to complete valuations.

I am sure your approach has been very soft and constructive, but I wanted to quickly remind everyone this is probably item number 14 on this person's list.  

(assuming 100% free and clear) How much equity would dictate using a more creative approach (lease option, etc.)? 

Your biggest challenge beyond correct comps is time.