A market downtown in the first few years of retirement, combined with regular withdrawals, can permanently damage a portfolio's ability to sustain income over time. The same downturn occurring 10 or 15 years later, when withdrawals have already been funded by earlier growth, does far less harm.
At lower portfolio sizes, income investing feels like something of a compromise. A 4% yield on $200,000 gives you $8,000 a year, which is barely $667 a month, so it's supplemental income at best. However, jump up to $500,000, even a moderate 5% blended yield can produce $25,000 a year, or right around $2,080 monthly.
When it comes to Social Security, your filing age matters for a big reason - it helps determine how much of a monthly paycheck you get. If you wait until full retirement age (FRA) to claim Social Security, for example, you'll get your monthly benefit without a reduction. If you file before FRA, you'll have to accept a reduced monthly benefit for life. And if you file after FRA, your monthly benefit will be permanently boosted.