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In addition to the technical concerns of a PoS move, it will unleash a torrent of regulatory / legal issues vis-a-via "Howie Test / Securities" discussion.
This Gordian-knot of issues: (a) Gas fees, (b) Miner dissatisfaction, (c) Legal ramifications, and (d) Will It Work? provides a terrible risk profile, so I completely understand his reluctance to move forward and continual kicking can down the road strategy.
As it stands, if everything else goes "perfect" it probably still doesn't fix the gas fee issue...it seems to be a no-win situation frankly.