I have come across several companies like Legal Zoom, Zen Business and many others, some which I think want to overcharged me.  

To ensure you can apply the tax deductions against ordinary/active income, you have to materially participate in the STR business.

Or maybe your family business is property management ?

I work with some of the best in the business.

He wants to use the 50k to jumpstart fix and flip business 

I am hoping for any advice/insights on how to proceed.

Ensuring Clear Title make a research is the key, there are professional bidders or auction representatives who can bid on your behalf at auctions, Attend local auctions as an observer to gain firsthand experience and understanding of how they operate, As you proceed, always conduct thorough due diligence on properties of interest, including property inspections, financial analysis, and legal review.

In general though, you're able to directly offset your income from the active rental activity with the *losses* you take from the business, but once the business becomes profitable, this would also add to your taxable income. 

While demolition costs are nondeductible, a taxpayer may claim a loss deduction when the depreciable business property is retired from use in a trade or business or from use in the production of income.I would strongly advice talking with a real estate focused accountant here to help guide you.

People like to do business with people who do business, present a good deal, and you will have a long term buyer to work with!