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Portfolio Management Service from a full service broker takes care of all of that stuff. Depends what your time is worth I suppose viz. record keeping. I think I pay $350 pa per Portfolio (2 x Trust & SMSF). I used to think it was a rip, but as my number of holdings grow I am seeing the value in it!

To your first question, mine is pulled from aud acct and converted at bank rate, the exchange rate used is on trade confirmation. Second question ;https://www.ato.gov.au/General/Capital-gains-tax/In-detail/Shares,-units-and-similar-investments/Identifying-when-shares-or-units-were-acquired/...