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cenario $5$: Bartering Gone Wild

A group of professionals forms an elaborate barter network:

A dentist provides dental services.

A web designer builds websites.

A lawyer offers legal advice.

A massage therapist provides relaxation.

A chef provides private dining experiences.

No cash changes hands, only complex trades tracked through a custom point system.

One member has an NOL carryforward they'd like to utilize against the 'value' of their services... but how?

Other Income $($For Simplicity, Just Focus on One or Two Members$)$:

Web Designer: Wages $$50,000,$ Interest $$500$

Dentist: Sole Proprietorship loss $($$$20,000),$ Interest $$1,000$

Questions:

What are the major tax reporting hurdles for EACH participant in the barter network? How do they determine FMV and income?

Can an NOL carryforward even be applied in a barter situation? Explain the complexities.

Could the IRS potentially view this barter network as a sham, or an attempt to avoid taxes?