Not that I know of (via Calibre, at least).
Over the years, there's been a few custom wireless transfer scripts written for personal use by various people, but I've never used any of 'em, and not all of 'em may be handling PDOC/ASIN/thumbnail shenanigans properly. And all of 'em require a jailbroken device.
Take all that with a grain of salt, since I haven't been using a Kindle as a daily-driver for more than a few years now (and wireless transfer was never really on my radar).
(But, yeah, as you surmised, there is some trickery involved in the Calibre Kindle driver when using "Send To Device" over USB, in order to make it "just work"
).