They have special family boarding. My wife and I just pay for a single seat upgrade, and then hold a second for the late boarder. Would want to be up front anyway.

i honestly have a hard time believing this. i've flown southwest multiple times a year with my family for over a decade. we never pay for early check-in and we're always able to sit together in pairs, often no more than a couple rows apart. i can't remember the last time i checked in within an hour of check-in being unlocked and didn't get a B or even a high A. maybe it depends on the route?

Definitely depends on the route. I used to live in Indiana and flying out of Indy was as you described. I now live in Denver and I always need to upgrade if I want to guarantee sitting next to my wife.