On this episode of Simply Money presented by Allworth Financial, Bob and Brian put your financial instincts to the test with a series of real-world scenarios that reveal who really comes out ahead—from high earners versus high savers to paying off your mortgage versus investing, maximizing guaranteed retirement income, and using tax-loss harvesting to keep more of what you earn. Plus, they explore whether leaving a bigger inheritance is always the best legacy—and why thoughtful financial planning often beats a bigger pile of money.