I bought mine from scAmazon. I see where it clearly states the $299 update in your screenshot as well
I get what you're saying and I did see the one free year of software updates. I've also never owned a scan tool that has a million stupid updates every time I power it on. Not ******** on the product as a whole, just not a huge fan of the little things. It does its job. It's programmed every tpms sensor I've needed it to, and it even pointed out my bad airbag sensor on my avalanche. All in all, it's ok I guess.
My complaints are likely self inflicted from lack of research and buying on a whim.