I've been using both these week for very different purposes, and I really think it comes down to your needs. But let's talk about some things I like about each of the devices:
The Chromebook Flip has it's own, proprietary charging brick, like almost every laptop out there. USB charging would be nice, to bring less stuff while traveling, But you can't have everything, no? The Tab A uses a regular micro usb port, which is super convenient as I can use one cable to charge both phone and tablet. Both devices take forever to charge up, usually I let them charge up overnight. I really miss the fast charge on the Galaxy S6, that's *bloody* fast!
One reason why I'm so enamored to the Tab A is the size! With the factory "book cover", it feels very well balanced, almost like a large kindle. Don't get me wrong though, holding a kindle for long reading sessions - fine. I'd get a stiff arm the few times I tried holding the Tab A up, and that's with the lighter, 8in screen!
And of course, the Tablet doesn't come with a keyboard, though any bluetooth keyboard can hook up to it.
The chromebook's really good for typing. Heck, since I've now been typing more on the chromebook than my macbook, I've had to re-calibrate my left hand when I was writing this post (on my mac), as I no longer have the Ctrl/Alt buttons at the bottom left of the keyboard. Just a few minutes ago, I was like... how do I jump from word to word again? On my mac I use my thumb to hold down the alt/option key; on the chromebook it's my little finger on the ctrl key. Blargh.
VLC definitely runs better on Android. Some very old files I can't playback on the chromebook play back fine on the tablet, or the desktop vlc. Something about the chromebook flip: Supposedly it only takes 64gb sdcards, whilst the Tab A can take up to 128gb.
I still feel dirty when I say out loud or type "apps". Ewww. Can't explain why. But anyways. The play store is definitely more vibrant than the chrome store. That's one major thing when I was hunting for games. Definitely much more choice - though not necessarily better games - on the play store.
The chromebook does zero to login screen in under 10 seconds, though it does take some time to churn when loading up google docs. And google docs does churn alot when your word counts go into 5 digits. And that's on my macbook - I haven't reached that many words on my chromebook yet, but I can foresee myself splitting up into several chapters per document.
The Tab A is the regular android bootup, but, how often do you reboot a tablet anyways? I rarely reboot my tablets. Pretty sure my mini's been online several months since the last ios update. Phone on the other hand, would do good to reboot ever so often - never know when a wakelock spike would come in *sigh*
I appear to be rambling now, and am actually quite tired, so I'm going to end this pretty pointless post right here. Good night!