I am risk averse by nature, but also have the fear of missing out.

Good morning Joe –The first question is whether the property securing the loan is “residential real estate” as that term is defined in Oregon Revised Statutes (ORS) chapter 86A, The mortgage lender licensing requirements contained in ORS chapter 86A are triggered by the character of the property rather than the nature of the loan (i.e., the real estate transaction involves "a mortgage, deed of trust, purchase money security interest arising under an installment sales contract, or equivalent consensual security interest . . . upon which four or fewer residential dwelling units are planned or situated, including but not limited to individual units or condominiums and cooperatives.

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.