If you want to participate in these programs, all I can say is, it’s your money, not mine.
Charging $25 to check you in ahead of time for a meaningless boarding pass number. Southwest will sell you an EarlyBird checkin service that automatically checks you in for a boarding pass and retrieves your boarding pass number 12 hours before the general public is allowed to check in manually. I never pay this fee, I just check myself in on time. Why? Because your boarding pass number never guarantees anything. Last week I managed to get boarding pass number A1 on a flight out of St Louis (I don’t normally buy Business Select, but in this case it was the only fare available) and although I was the first to board, there were 33 through passengers already seated when I got on, so none of the good seats were available. A low boarding pass number gets you very little in terms of seat selection unless you are boarding an originating flight with no through passengers. If you are thinking that Southwest only charges $12.50 for Early Bird, you’re right, except that they charge it both ways. So if you have a roundtrip ticket, it’s $25.
Charging $40 to sell you a slot in the Business Select boarding group. Southwest will also let you pay $40 to jump the line and get into the A1-15 group if there are any slots available*. Curiously, Southwest doesn’t seem to have an official name for this service, but it is generally referred to as an Early Boarding Option. You have to pay at the boarding gate and it only becomes available 45 minutes prior to boarding. (Commencing sales 45 minutes prior to the flight is somewhat amusing to me – Southwest gates are rarely manned at the 45 minute mark.) The one exception I would make for paying this fee is if I got stuck with a C boarding pass on a long, full flight. So if you forgot to check in on time for a full flight and you can’t tolerate the middle seat, this one could be worth it.
*Slots A1-15 are blocked out for passengers buying Business Select (the most expensive) tickets. If only 10 passengers have bought Business Select tickets on your flight, it means there are 5 slots still open in A1-15. If you watch the boarding process closely next time you fly, you will likely see that there are less than 15 people in the A1-15 boarding group. Those empty slots look like dollar signs to Southwest, hence this opportunity to pay more.
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