The "rebook-to-get-things-to-work" thing is really reminding me of our SSR checkin on 2/15 and 16. And rebooking wasn't the first problem. I'll try to be brief and keep it to what *feels* relevant and maybe related, maybe a precursor to the OP's problem.
Did online checkin as far in advance as the site would let me, but our packet was only done the hour or so before we physically got there, which we know because the CM next to "ours" said she had just done our packet and went to get it. Despite the online checkin process, the CM said that our CC info was "lost". (except that the sticker on the packet said that CC info was received) We opted to leave the CC off of the account since it was a mixed family trip and I didn't want to cause any mixups or messups.
All KTTW were created at that time. We went off to AK for the day.
Got an urgent phone message not that long after telling us to come back and have all KTTWs redone. We were in AK and decided it could be taken care of later. Our family wouldn't arrive until late evening and we had no urgency. We got a text later of our room number.
When we got back, we were told by the lobby concierge that we had gotten "stuck" in an "checkin glitch", where the system doesn't know that we have fully checked in, and the KTTWs won't work. Weird, since I had *just* used my KTTW to get in the "returning guests" gate, but OK.
So they redid all the cards.
Should have been the end of the story, BUT our 2 bedroom villa (1135) was horribly mildewy, and after one rotten night (where even the not-sensitives in our group were complaining) we switched rooms. (they offered us a grand villa during the first conversation DH had with a night manager, but we declined, not wanting more than what we were due, we would wait for another 2 bedroom. the manager was surprised, and offered an amount of room credit that DH accepted.)
So the next day we switched rooms, after meeting with the housekeeping manager who nearly wrapped crime scene tape around the villa once he came in to the room and sniffed the air. Uh oh, getting off track.
OK the room switch was done, we got settled in again. We had a weekend of no parks planned, so we went to the Paddock Pool. DH went up to the front desk to put charging onto his and my KTTW, because there's no way to access the credit if you don't have charging put on your cards (which is the most ridiculous thing ever but that's a huge digression).
That process took 2 hours. And ultimately involved *rebooking the room*. Because we got stuck in a glitch, and it WOULD NOT reprint KTTWs unless they did that. Absolutely would not. It all took so long, and took DH so many trips back to AP to try to make purchases that finally the CM started going with him, and ultimately they increased the room credit voluntarily by half again. And they tossed in two refillable mugs.
This whole "keys won't print unless you rebook" thing sounds mighty familiar. Part of me wonders if there was some sort of something that went live but shouldn't have on that day (checked in first on 2/15, but this part took place 2/16). No way to find out, but it's interesting all the same.
Should it be like this? No, I don't think so. But it seems to BE so.