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It's like life is a realtime monopoly game I'm learning tactics all the time.
To be clear, I assume the company wasn't wholly owned by him, correct? Because if it was, it wouldn't be a conflict of interest.
I think there are many changes coming down the pipeline as governments start running out of money. Capital gains tax normalization, capital gains tax treated as income every year instead of at a 'event' when you sell. An effective wealth tax by taxing a percentage of property value. Once those are in place I think they'll crack down on the creative use of corporations to minimize tax.
This is common and legal structure designed to, among other things, reduce taxes owed. It only becomes a problem if the business has shareholders who are not participating in the scheme to shift money to the land company.
Buy the building or even lease it with a sublet clause using a separate entity, and then lease/sublease the space to the cannabis business with the lease fee being, for example, "90% of gross revenue". I'm not sure on the details of how operating funds were pushed back in.