How should taxes affect my decision about simplifying an old or overly complicated investment portfolio?

For this planning decision, identify the purpose, tax status, fees, asset class, and concentration of each holding, then compare the combined allocation with the household's goals and risk capacity. Within the broader financial plan, rebalancing inside tax deferred accounts may avoid current capital gains, while taxable accounts require attention to basis and tax consequences. As part of the financial analysis, use after tax and after fee numbers when comparing options because headline returns or payments can hide the real tradeoff.