We didn't take the loss through the years for the original cost, just the operating cost like taxes and utilities. 

It may be accurate to say that I don't yet understand how to properly utilize the equity I've built in my properties, but I plan to learn.

From what I've read and through my brief interaction with a lender, the rentals need to be traditional and I need to provide a copy of the lease.I know Quicken Loans allows refinancing through Airbnb income alone but is the rest of the industry just too far behind?

They usually pay all utilities.

They will ask for telephone bills, rental history, utility bills, etc. to show you make your payments on time. 

In the banking industry we call that an "overlay". 

If you pay all your rental bills thru this account (I would pay your personal portion of rent/utilities to this account each month.

A good dynamic pricing utility like wheelhouse or pricelabs can optimize price and minimum stays throughout the year.

I would be careful about the owner utility paying. 

He believes in solid companies like power, steel, etc, companies with a history of profitability and reserves in the ground figuratively or literally, depending on the industry.