For your payout, I don't know the full story but Airbnb doesn't cover extra fees including cleaning fees.

I'd like to bring him in to assist with the renovation expertise as well as access he has offered to his labor pool.

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

Glazing in walls, enclosures or fences containing or facing hot tubs, spas, whirlpools, saunas, steam rooms, bathtubs, showers and indoor or outdoor swimming pools where the bottom exposed edge of the glazing is less than 60 inches (1524 mm) measured vertically above any standing or walking surface shall be considered to be a hazardous location.

I would have recommended getting it cleaned out.

.- Full time maintenance, reservations, cleaning staff- Additional marketing budgets and resources.This is a brief list but a good PM can make more revenue than you can and can offset their fee. 

My plan is to add 2 - 6 shipping container type of small houses and an above ground pool at some point to make at least a section of the property short/mid term rentals.

After waiting out a lengthy eviction and doing nothing more than a clean-out, we listed it with a realtor—and walked away with just shy of $200K in profits!

We could use a new cleaning company though.  

While it may seem daunting at first, beginning with a clean slate allows you to establish clear expectations and build a strong landlord-tenant relationship from the outset.