A financial advisor or real estate pro could help you map it all out more concretely.If I were in your shoes, I'd probably lean towards selling and reinvesting into some more diverse assets, or just more properties, but that's just me. 

In previous roles, I was responsible for the asset management, capital improvement, repair, and maintenance of an ANG Fighter Base worth over $400M.

It's important to understand the zoning/code requirements and obtain all necessary permitting if you intend on operating your real estate as STR anywhere in the country.

Additionally, most of the costs to make an asset ready for it's intended business use are capitalized and part of the cost of the asset. 

Because of the nature of a tax lien, it would be difficult to obtain financing from a commercial lender secured by the tax lien itself.  

Whats a typical multiple for such asset?

Has anyone had any luck obtaining legal counsel and fighting this?  

There are companies that syndicate nearly every asset type in nearly every market in the country.

Hypothetically, if I found a property with strong rental demand, the income could cover loan payments, operating expenses, and generate a modest positive cash flow.While this example involves upfront risks, the idea would be to leverage my father’s expertise as a contractor to minimize renovation costs, boost the property’s value, and create a long-term asset that appreciates over time.

No deal(s) just insights & offers to obtain a premium membership that cost ten times the membership you already have (with monthly or annual dues).