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

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.

I work with some of the best in the 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 ?

It's a matter of the systems they have in place to limit the risk of things like you describe form happening..

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.

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. 

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!