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I don't watch every single vendor; so this is just my opinion. You'll have to do your own research to be sure; but I don't think there is anything more recent than what you already have which fits every one of your criteria.
There might be ones which are android (so you can have Calibre Companion), and a headphone jack... but not physical buttons. (Likebook?) Or there might be ones which have physical buttons and TTS via headphone jack ... but aren't Android/no Calibre Companion (Pocketbook Touch HD2 or HD3?).
I can say that my current favorite is the Pocketbook Touch HD3. It can do TTS via Bluetooth; it doesn't have a headphone jack built-in, but it does come with a dongle adapter. It does have physical buttons. I can't install the android app for Calibre Companion... but I can get to my Calibre library via the Web Browser and download books that way. (or of course, plugging it in/side loading over usb from Calibre on the computer itself)
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