As a Realtor you might want to consider an alternative game plan.

value adds, flipping, alternate rent models such as STR, MTR, rent by room  can help with the return. 

Alternatively, DSCR ratios may not work out due to efforts to maximize the loan amount and avoid additional cash contributions. 

When you counter, or make a substitute offer after the seller says no to your original offer, all you're doing is telling the seller your first offer won't your real offer, so the seller will keep countering until the squeeze you to death.Make one offer, no counters, no alternates, and they either accept it or they don't. 

And here's a really good kicker, if trucking is in the tanks, all the trucks have to be parked right?

Explore alternative options like hard money loans (fast but high-interest), seeking private investors, or obtaining a business line of credit if your business generates income.

Alternatively, what's the best way for my friend to get their funds back without any tax implications (if any) for him and business?

In six months, you will have done more research than most on these two alternatives, and you will have your answer. 

In that I would not own the home in my name (the trust would) under those assumptions.Is this even a reasonable strategy to jump start a real estate investment portfolio, any alternative ideas are welcome.I hope I have stated this with enough clarity, Please let me know if additional information is required to answer the question.

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