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I went with the Roku Ultra earlier this year as my first Roku device because I knew I'd be upgrading to 4K. I ended up with a Roku 4K TV (TCL) so it didn't really matter, but I still like the Roku Ultra better than any of the others I have (2 x Roku TCL 4K TVs, and 2 x Roku Express) because I really like that the controller comes with a headphone jack. Those are two main points for Ultra (4K, headphone jack remote) vs. Express (none of those things). Ultra also has a media card reader that I've used to stream online courses downloaded from the internet (that didn't have a Roku app).
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