I know this is a very delayed answer, but we’ve asked several GS agents during the past month due to a sort-of similar situation and they told us that the ‘free’ HHN ticket for Premiere pass holders is based on season and not year.
Long story short, we renewed our AP (Premiere) last August and attended HHN in September. It just so happened when we renewed, they had the 3 months free promo. We’ve been told by various GS members that, yes, we may attend this year for the free night. Our pass expires early November of this year. When I view my pass in the app it also states HHN ticket:
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Maybe double check with GS, but I’m thinking you’ll be fine (hopefully). I think it’s just a fluky type of situation due to the timing and the 15 month promo. Otherwise we would’ve renewed as usual this month and would’ve had the free HHN ticket anyways.