The Instructions shown in next paragraph below says, I should be able to select a contentious range of transactions using shift key. Unless I don't know how to hold down the shift key and click on a Mac, it does not work
To select multiple transactions in Quicken Simplifi, navigate to your Transaction Activity, find the checkbox to the left of each transaction you want to select, and click it to mark it. You can also hold the Shift key and click the first and last transaction to select a range, or hold the Ctrl key (Windows) or Command key (Mac) to select individual, non-consecutive transactions. Once selected, you can click the pencil icon in the upper right to open the bulk edit menu and make changes, like recategorizing.