SoSquidTaste
Not that I don't agree with your original point (I do), but I think the above is perhaps a relevant peek into the author's mindset.
$7.99/mo had that perfect impulse-buy attraction to it, and got me into the game. But after using it and seeing the kind of content they've been building (even despite the content that they've lost, and will contractually have to lose later), $10/mo still seems pretty palatable to me too.
My gut agrees with this implementation, but my gut also forgets that my brain sees similar checkboxes on, for example, Expedia right now about flight/trip insurance, blows a raspberry, and declines.
I feel like there's got to be a way to roll this into the current online bookings workflow that still communicates the seemingly-novel way that a service like LevelSkies works so that it doesn't become another ignored checkbox.
I like that this service presumably looks at similar data, but finds a way to help aforementioned average consumer directly benefit from the data!
EDIT: Oh whoa. I didn't see bluedevil2k's post (https://news.ycombinator.com/item?id=7623622) about Bing pulling the flight data stuff. Interesting and somewhat troubling! I also hope that LevelSkies has some hedging in place, but I think it also makes their service seem even more important.