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I'm planning to transfer 2 x $100 monthly at 15th and 29th each month. Does it make sense to do it this way actually?
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You can set up 2 standing instructions from your bank to transfer on 15th & 29th. (Do note that it will take them some time for the amount to be reflected.)
If you have multiple portfolios, the money from each transfer will be spilt to the different portfolios accordingly.