Quicken handles bookkeeping, investment entries including reinvested dividends and lot purchases and sales, connects to get Market-quotes real time to give FMV on the reporting relative to the basis and shows gain/loss in reporting, allows you to use the same functions to set a historic date for Market price on that historic date to correct or adjust for basis, has recurring transactions that you also can use for electronic payments, banks provide more support for connectivity to Quicken than QB.