The ATO does have a 1 year delineation for 50% CGT discount on sale of shares...
BUT I'm pretty sure this is over-ridden by being classified as a trading 'business'.
That is, if you include a particular stock in your business accounts and hold it for years, and want to then effectively remove it from your trading business and re-classify it as an investment... you will have to pay full CGT, whether or not you actually sell the shares.
The CGT 'event' will be considered to have happened at the market price when the reclassification occurred. Or the sale price if you actually sell the shares.
That's how I understand it, anyway.
Whenever I'm in doubt about which way a ruling could go, I always think:
"Which outcome would benefit the ATO the most, and me the least...?"
