Work with your commercial lender and see if you can self finance, by cross collateralizing your existing portfolio.

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

One lot has a 2 bed and one bath cottage that was an existing STR. 

You can cover the wire mesh with drywall patches (they tape on wall and across the wire, white/paintable, different sizes) as the wire mesh is what will prevent the rats from eating their way into the property (the covering material is cosmetic only).

The sale proceeds likely won't fully cover my loan.I have a few questions: What documents will I need to complete the buyout of the first lender?

Oftentimes my initial consultation call with a potential client runs 1 hr and that still doesn't give me enough time to cover everything about the STR market on O'ahu.  1.  

And all the tenants' security deposits and all the buyers'Earnest Money Deposits don't need my asset protection, as they are not my funds, and are certainly not covered by any of our Umbrella Insurance Policies. 

Btw, I learned about this from a book about the career of Harold Helmsley (pre Leona!)

If any need for boots on the ground ever exists for you, I would be happy to assist or brainstorm.

I managed STR with my sister twenty years ago before Airbnb existed.