This is the best way to build a natural, organic relationship with someone that could turn into a mentorship.

Next, what underwriting criteria do we need to watch out (or plan) for, or have the largest impact on a re-fi of this nature?

Mother Nature has no respect for your plans so all you can do is design around her. 

I am a non-confrontational person by nature and it has taken me time to grow a thicker skin.

Take a weekend and drive around.....lots of natural attractions and cool little mining and cowboy towns. 

My natural inclination would be to use commissions to reduce prices and avoid taxation or split 50 50.

On some, I purchased and then renovated years later, or renovated over time, or lived in them / renovated over time / and sold them tax free, and they naturally appreciated as expected from purchasing in growing areas, and they went through spurts of larger appreciation...everything stacks over time (if you're invested).

Personally, I think some of his points are a little excessive, but not everybody is naturally financially literate.

They should of told me it would be difficult :) Finding a home that makes sense has been a natural challenge.  

The nature of many deals won't make sense at anything less than 25% down.