You are right that it's daunting to select the best time to start SS, with so many moving parts. Mostly I don't have the date of death info. One SSA rep said to me, "I'm not supposed to say this, but why are you leaving money on the table by starting later?" Many of my rural clients are physical laborers who wear out their bodies by their early sixties, and their income stream stops. Other well-to-do clients have to consider the Medicare premium hit if their AGI gets too high. One client moves funds from IRA to Roth only up to the Medicare cliff (something like $78K per spouse?). So you are right, each situation needs to be customized, but 90% of the time it's self-evident among my clients. (Hw, I was surprised by two of my clients aged 70+ who were still working and put off starting their SS benefits out of ignorance.)