Consider converting higher-priced stocks to potentially benefit from tax increases in the future when tax brackets might increase. The current tax structure will change in 2026, eliminating the need to consider the length of time you've held the stocks. Consult with a CPA to determine the optimal amount of conversion and focus on converting larger sums at once to benefit from the five-year rule, which starts with each conversion. This strategic approach allows for maximizing the benefits without impacting your tax bracket significantly.