pinniped

Good job, OP, for not backing down. ^

I have sympathy for, and am usually willing to work with, people who use common sense when they want to arrange a simple seat swap.

On a legacy carrier, that means offering up a better seat to the swappee, taking the worse one in exchange for getting the swap. On Southwest, that means at most saving 1 middle seat in the back of the plane.

I have zero sympathy for, and might come off a bit d!ckish towards, people who fail to use common sense and are attempting to milk both an "upgrade" and two seats together.

On Southwest, there's really no excuse to ever need to violate this basic principle: their system is set up such that anyone can simply check in at the correct time and obtain decent BP's. Even when I'm traveling with 4 people, no A-list, no EBCI, on a sold-out flight out of MCI with a bunch of thru pax, a high-A or low-B boarding pass gets some decent seats in the back.

If you're out of the country, airborne, at sea, or somewhere in the deep wilderness 24 hours prior to your flight, then just invest the $20 to get two EBCI check-ins. Piece of cake.

If you get irropped or buy your tickets inside 24 hours, then everybody in your traveling party will need to familiarize themselves with emergency in-flight survival technologies such as newspapers and magazines. But that would also be true on a legacy, even with elite status.