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I did consider that a possibility, so I watched a couple of other videos. In those ones, when the guest says something he agrees with, he doesn't challenge it. So I don't think it is a case of him playing devil's advocate.To some extent he was trying to counterpoint William Legate who is known for mounting campaigns and court cases against Trump.
Also bear in mind, we can assume he's a Republican because he supported Marco Rubio in the 2016 primaries. The path from supporting a "normal" GOP candidate to getting on the "burn-it-down" train is now pretty well-established with right-wingers going full on for Trump.
The big one though is he said he doesn't think Trump is malevolent. Just take a minute to think of all the stuff Trump's done, tried to do, said, tried to say, inspired, etc. And Dylan doesn't think that's malevolent? There's only one group of people who don't think Trump is malevolent - Trump supporters.
And yes, he could've voted in 2016, but he couldn't be bothered to. Said he had a workout and couldn't be bothered to queue or something.