Are they leaning in to it or are they forced to fit in the disclaimer?
Seems like the strategy of the ad is to repeat the word "Free" so much people don't remember the rest and to make it seem like the disclaimer is meaningless. Even with it, it's still free.
Probably a bit of both. What the commenter is describing is a textbook social proof tactic. "Hey, I like free stuff and taxes make me feel like a bit of a doofus, just like that guy. And like that guy, I see myself as the clever sort of person that isn't fooled by fine print. That free Turbo Tax program sounds awfully useful and free for people like me!" And Intuit can also point to that commercial and say "how is this trying to disguise the proof?" and they'd be right. They're just also trying to make it feel free still by making it free for a relatable character.
Sounds hokey but that sort of shit has been the bread and butter of advertising since forever. A vanishingly small percentage of people are anywhere close to as rational as they think they are when buying things. Many of the most self-assuredly "skeptical, rational, well-researched consumer" types get totally snowed by the simplest marketing ideas because they're looking for sales bullshit they can empirically disprove, and most marketing is influencing people in a way that makes them think they came to the conclusion independently.
Seems like the strategy of the ad is to repeat the word "Free" so much people don't remember the rest and to make it seem like the disclaimer is meaningless. Even with it, it's still free.