it's literally one of the easiest things for the ato to track, they will know about the sale.... he has to make deductions, ordinary income losses or capital losses to offset against that whopping capital gain....doubt he'd have a massive amount of losses... i'm with jase... you can't just make sh!t disappear.... they generally just suck it up and know they lose 23.5% of their ultimate capital gain... directors and high wealth individuals are fairly obvious audit targets too...
Ann: Change of Director's Interest Notice - PH, page-29
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