Yes to both. He's not stupid.
And a bit of that too.
He's doing several things at the same time, because he's smart. Many longtime CM's have left Disney lately, a trend the whole country has been in with The Great Resignation of 2021-2022. Disney's got to retain what talent they have left, and attract new talent that understands the difference between Disneyland and David's Bridal, or Disney World and Dunkin'.
Disney's theme park division has historically treated its Parks employees far worse and as clear second-class corporate citizens compared to the Burbank and Glendale groups. Josh appears to understand that, and pre-Covid he was trying desperately to improve the Cast experience at Disneyland.
He's got a bit of a thankless job right now, reporting to and having to publicly support the cheap and charmless and clueless Bob Chapek. But Josh knows there will either be a time when Bob Chapek is no longer with Disney, or a time when Josh D'Amaro is no longer with Disney. Either way, Josh is strengthening and solidying his own personal brand with videos like this. Because he's not stupid.
All that said, I fear this will only cement his cringey position as the Cool Dad Exec in the skinny jeans.