Thank you both for the DPs. You motivated me to HUCA once again and this time the agent did it no problem! I guess the 4th time's a charm. It's kind of baffling the amount of inconsistent messages though. I've also been asking about getting points for free night certificates that are close to expiring and I've gotten the following answers:

1. No way, must use by expiration date or you're SOL.
2. They might give partial points after expiration but only in dire circumstances like a doctor's note saying you're not allowed to fly.
3. Of course! No problem, you'll always have the option of getting partial points up to 90 days after expiration.

I like option 3, just hope I can find an agent to give that same answer if my cert expires.