Yes, this sounds a little odd but bare with me. I'm selling my IP next financial year and will be hit with a significant capital gains bill. I'll also be (I hope) getting good income from investments that are being put into place now. So I'll be up for a hefty payment. This financial year, however, I expect to have no taxable income. I was planning on putting significant funds into the Vanguard Wholesale Australian Share fund as a buy and hold to deliver ongoing dividends. But a clever (maybe) financial friend suggested something different at the pub tonight. He said I should try for a 'profitable capital loss'. Instead of the Wholesale fund (which distributes quarterly) he reckons I should buy into the retail fund which distributes bi-annually. Given the dividend payout of Oz companies this year, the June distribution is likely to be very large. Equally likely is that the price of the fund will drop straight afterwards. His suggestion is that if it does, I sell straight away and take the capital loss which I can then use against my capital gain from the IP. So I get the (mostly franked) distribution when tax is at its lowest, and can reduce the CGT when tax is higher. Beer made it seem to make sense. Does it?