So for those with the Hilton Aspire, there shouldn't be any need to play these shenanigans going forward, now that the credit has shifted to $50 per quarter and is good for all flight costs. For Southest, you should be able to buy a ticket for ideally slightly more than $50 (but for any amount really) and then just cancel it and have it refunded as a non-expiring Southwest flight credit to your Southwest account. I'm also experimenting to see if I can book a flight, and then cancel within 24 hours (which will fully refund to my Aspire), and see if they still process the $50 credit despite the refunded amount. Will let everyone know if I have success with that. I think it would be a more elegant solution for redeeming the $50 quarterly credit than having a bunch of Southwest flight credits to keep track of and use.