Oh my goodness, what a rollercoaster!
Return flight Grand Cayman to BWI didn't release a non-stop (even though they were doing one non-stop each Saturday for several weeks prior). Connecting flights are long and expensive (24k points each when outbound were 11k) but I start booking. I enter my travelers, travel funds, hit purchase, nothing. Page refreshes for a bit then stays on that same page, neither purchases nor gives me an error as to why.
I try again on a different, incognito browser, but now points are up to 27K each!! It will not go through with my travel funds, so I give up and put the full taxes and fees ($272.58 because GCM has a bunch of fees) on a card. Ugh.
I call SW to see if there's anything they can do. After an hour of work, a very kind and patient customer rep is able to assist me with getting the 24k point booking and applying travel funds as well. Apparently, in my account I have Hubby's full middle name but in his he only has his middle initial saved. So, initial versus full name was hanging up his travel funds but it didn't tell me that on the page.
I'm still bummed about the cost and the connection, but at least I got back the 9k points difference and was able to use $120 in travel funds against the taxes! In the meantime, WGA are gone for the day, so 24k is now looking cheap compared to the 40k Anytimes.