(Image credit: Getty Images) The most stressful Social Security meetings I have aren't about whether 62, 67 or 70 is "best." They're about the week someone planned to file … and suddenly can't. A few months ago, a client — let's call him Jeff — called me from the back seat of an Uber on the way to Chicago's O'Hare airport. Jeff and his wife are the kind of people who do retirement the way they do travel: With spreadsheets, backups and confirmed reservations. From just $107.88 $24.99 for Kiplinger Personal Finance Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues CLICK FOR FREE ISSUE Sign up for Kiplinger’s Free Newsletters Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail. Profit and prosper with the best of expert advice - straight to your e-mail. Their Social Security claiming strategy was intentional. They had a date circled on the calendar.…