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reinvesting dividends requires 2 transactions to increase # of shares

unknown

Reinvesting Dividends transaction (TC) does not increase the # of shares for mutual funds, nor for CDs(since they are not handled as a CD!). You must make a 2nd TC, using a different date. I recommend showing zero dollars so as to not screw up total dividends received.
With CDs I classified them as money market instruments and was then allowed to enter them once in order to increase the balance. This is of course doing reinvest interest and you show it as shares, not balance.l
I have changed all the mutual funds to an asset class of money market, but have not yet tried any TC to see if the situation is corrected. I have not looked into trying stocks!

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unknown

Quicken Premier 2018 for Mac. The problem does not exist if using the Windows version; i.e., Premier 2018

unknown

It reads as if placeholder transactions only apply if online with the FI. I enter transactions manually; i.e., am not online with any FI.