Will Apple allow their trademark to be used in this way? Or does it fall under the “____ sucks” provision of free speech?
Trademarks are intended to provide consumers with the confidence that the products they're buying really come from the producer they claim to come from. As such, you're prohibited from assembling your own computer and branding it Apple; you've never been prohibited from referring to Apple.
"Even if [the] use is commercial, it must still lead to a likelihood of confusion to be violative of the Lanham Act. 15 U.S.C. § 1114(1). In Planned Parenthood, the defendant used the plaintiff's trade name as a domain name, without the qualifying moniker 'sucks,' or any other such addendum to indicate that the plaintiff was not the proprietor of the website. In contrast, 'taubmansucks.com' removes any confusion as to source. We find no possibility of confusion and no Lanham Act violation."
In summary:
"If “Super Bowl” is used by an individual or business to describe the event and not used for commercial intent, then individuals and businesses can use the term. For example, a grocery store can say “Make sure to stock up on chips for the Super Bowl” but the store cannot say they are the “Official Super Bowl Chip Stop.”"
That said, you can just avoid infringing entirely by calling it The Big Game
Maybe everyone is afraid to be first into the breach, like so many avoided using "Happy Birthday to You" for decades in fear of the bogus, broad copyright claim