Specifically, more on your partnership and the roles played, the funding (saw in your original post you were exploring options), and how you are managing the properties.

I just don’t know what the long term play is with these.

If you don't have the vision to have MANY airbnbs in Champaign I'd suggest figuring out a strategy you have a long term big vision.Pros:  High cash flow (if done right), typically properties are oddly better-taken care of, sexyCons:  Management/system intensive, always on call, regulation can change things instantly  

What role does being named "Additional Insured" play within the context of a Lender?

You might have been able to get the tax sale cancelled in not, but at the same time you might have made out just as well the way it played out.   

I feel there’s too many variables that can come in play.

You can even have both meet and play nice in the sandbox.

If any issues were to come up, you can easily call a vendor you trust to remedy the solution.Short term rentals are obviously more time intensive but even then they can be easy to manage.

A little capital intensive but still did ok. 

@Desstani R.Investing in single family homes for short-term rentals can generate higher cash flow and flexibility, but can be management-intensive.