.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

You post, and potential residents will reach out...or maybe they don't.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

All of the tools that you use to try to figure out if a potential tenant will be a "good" tenant revolves around trying to answer those 3 questions.

Any advice on how to navigate this while keeping the deal intact or potential transfer of partners would be greatly appreciated!

I will be living in the guest house, while renting out the main.Both units are without washer and dryer units, my question is, do I supply them in the main house; or let potential tenants figure that one out?

The Highway 64 property presented a great opportunity due to its low acquisition cost and potential for substantial value increase.

It's the conclusion you came to before you wrote the post I know but bringing up the challenges might make you realize that you might have to offer a heck of a good deal to attract a potential partner.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

Owner occupied loans have allowed us to purchase properties in markets with heavy appreciation, and potential for huge rent increases.