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Originally posted by All4One ↑

Long Pier

In Australia if you have an asset that will attract CGT and you sell it you will be liable for the CGT owed from the sale whether you sell it and buy it back or not the CGT is due on the sale.
As for settlement date the sale will probably be judged sold at settlement imo, I dont really know though but that makes sense.
I would say what are dancing your way around is can you take the sale forward to next years tax.
For this reason some people actually go out of their way to sell shares at a loss near tax time and sell them from one company to another that is owned by the same legal entity. IE if you run a family fund that fund can buy and sell shares but another company registered under the fund can also buy and sell shares but there has to be what is called an "Arms length"between the sales most likely.
In any case if you had a fund none of this would be a problem because you can disberse any profit to the beneficiaries of the fund, ie your kids should you have some.

Please DO NOT take this as legal advice as Im am not a lawyer, not an accountant or a finance worker in any way shape or form.
This is just from my own experience with a family fund.

The short answer is mate. Ring up your accountant and let them tell you then you will avoid very costly mistakes. I can tell you if you make a mistake the ATO will fall on you like a ton of cow manure and audit the crap out of you for years.
Been there and done that which is why I use a good accountant and the fees are tax deductible.

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As for settlement date the sale will probably be judged sold at settlement imo, I dont really know though but that makes sense.

That is incorrect. As discussed previously, the trade date is the date used for tax purposes, not the settlement date.

That is the reason that the last trading date of the tax year (today) can be quite different from normal trading days, as a lot of trades are related to people buying/selling for tax related issues (such as realising losses to write off against gains for the year etc.).