Yes, the PA's will be there handing out cards and trying to get your business as the fire is being put out. 

Hi Lahiru,Great question, if your wife has been considered to meet the threshold for "Material Participation" in the business, then you would be able to take these losses.

Reporting the mortgage interest on the return should be done with care, as the IRS does not have a copy of Form 1098 under your SSN (or EIN if business) reporting the interest.

TLDR: It was a fantastic workshop that will enhance my business, but he pitches his Big Dog program that costs anywhere from $20k-$60k.

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

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

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 

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.