If you are referring to the companion pass through the Bank of America Alaska Airlines Visa, it is only valid on a paid ticket. If you use miles to get a ticket, you can't use a companion pass to get a second ticket.
You might be better off finding a condo through VRBO, which will cut down on meal expenses, than to stay in upscale hotels with pricey restaurants, parking and resort fees, etc. (Then you could use your SPG Amex points for miles for the flights.)
I tried to use hotel points for a Maui trip in November, and finally decided it was actually better to just pay for a condo.
With the Chase Hyatt card, you'll get two separate Hyatt certificates for one night each, so I'd think that you could use them for 2 rooms on the same night, but I'd recommend confirming with Hyatt.
Chase also has a Fairmont card with 2 free nights, but I wasn't able to get the nights that I needed at the Fairmont in Maui in November, so I don't know if you'd have much luck in February -- and it's not in Kaanapali.
Sweet! Thanks for the heads up. VBRO is the other option I'm competing with. My mother-in-law has been living on that site, and has found some awesome deals, I was just seeing if I could make it happen for cheaper using points. But you're right, everything is going to be more expensive on a resort, and once you include the $180 per night, resort fees, gratuity, etc, might just be worth it to use VBRO and save the points for flights/car rental.
Honestly, if even one more person could churn, it would make the process MUCH simpler. But alas, 'tis not our lot.
I'm still open for suggestions, but will continue to price compare with VBRO. Thanks AAL!