re: How much of a "cushion" do you leave in your checking account after paying bills

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Its less of a headache unless it auto drafts if you dont have enough funds to cover normal bills(gotta watch fees tho here) then to constantly think about transferring money over.

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I would only need to transfer if an unexpected expense came up

When I get paid on the first I just move everything that was in the account the day before into savings.