The larger cash flow would enable me acquire more properties quicker. 

Each Son is in a different place in their life and has different views on what to ultimately do with the cabin.Options include:Start an LLC (Out of State) Like Maryland or Florida with no income taxThis would enable purchase of more vacation rentals in the area to be managed similarlyBuild additional properties on the land and expand + Rent out.Make the cabin available year round during Northern Wi which would require maintenance and updating.

If so, then sure, and I would like to use the same crystal ball as you are ... if not, then that is what that "R" is for, to guarantee the forced appreciation that enables the cash out refinance.

Technology advancements such as email, phone calls, skype has enabled communication with a remote CPA to be seamless.

Technology has enabled communication with a remote CPA through phone calls, emails, skype etc.

This enables lenders to keep an adequate supply of money for new loans.

@Chris SwindleMy first question to my investors (putting myself in your shoes from my perspective) would be your feedback is much appreciate and enables me to be of best service to you.

You run a business here, don't be an enabler. 

If not, I feel you are leaning too hard on being an enabler, which is never good in my opinion.

I advise my guests that they can use their own Directv, Dish, COX, Comcast account to enable other streaming functions if they desire.