Life is full of trade-offs—and nowhere is that more true than in financial planning. On today’s episode of Simply Money presented by Allworth Financial, Bob and Brian put a fun twist on tough money questions with a special “Would You Rather?” edition. Should you sell highly appreciated stock now and pay taxes, or hold and pass it to heirs with a step-up in basis? Is a bucket strategy better than a total-return approach? Would you move to a no-tax state or stay in Cincinnati for family ties? From direct indexing to Roth conversions, these choices could shape your wealth, your legacy, and your peace of mind.