All at Retirement: Exercise all your options in your final year of work. Pros: Simple to execute, aligns with retirement date, no multi-year planning needed. Cons: Could push you into a much higher tax bracket, especially with large gains; less flexibility.
Split Over 2 Years: Spread exercise across two calendar years to reduce the tax burden. Pros: Helps smooth out income to avoid top marginal tax rates; still relatively simple. Cons: Requires careful planning and potentially holding shares for part of the time.