It seems deliberately confusing to me since there is no fundamental difference between voting now and voting on the day of the deadline, but the way it’s discussed and referred to seems to imply that the correct day to vote would be waiting until the last minute instead of voting just getting it out of the way weeks ahead of time.
“Approaching 20 years” so exactly 20 years ago is 2004, which makes 5 elections not counting the present one: Bush Jr. 2.0, Obama, Obama 2.0, Trump, Biden. Figuring this person turned 18 and registered to vote in, say 2006 and missed voting in the 2004 election, that would be 18 years and 4 elections, this current one would be 5.