I think the worst part is the match from Southwest. I'm fine with the match if it guarantees him the exit row 17F on the 700's and nothing else same as Southwest. Moving up not so much should have to earn it.
If Alaska does give him the 50k(hope not) why not throw in some companion certs for making the switch, don't want him to have to go backwards.
Congrats, but do remember Alaska is starting to board like Southwest so get to the gate early so you get in your seat and hopefully get your bags(4) up early. Never mind you will be the person standing at the gate 1 hour before at the front remembering that A1 pick, just remember don't take the first available. You have to be assigned the seat. Who cares though everybody switches everybody these days.