Perhaps a love of money has less to do with its presence or absence, and more to do with its hold in our hearts. Maybe it has less to do with whether we have more or less money, and more to do with whether our thoughts, conversations, and budgets are excessively focused on it.
Paul’s plea is a plea for contentment and simplicity, not for relentless counting, budgeting, and price-checking. The goal is not to have very little money, but to think little of money.