Here are my thoughts as a Florida resident:
During the 2018 campaign, I was singularly unimpressed with DeSantis. His efforts to kiss up to Trump were
cringeworthy, and he mostly just came across as an empty suit. There's a good chance he would have lost to Andrew Gillum if Gillum a) wasn't under investigation by the FBI, and b) were better able to parry the "socialist" label.
Once DeSantis got into office, his first couple years were spent mostly moving toward the center, as others have outlined in this thread. At that point I started to reconsider him a little. I knew he was still very right-wing, but I realized he was a smart guy and a lot of the shenanigans during the campaign may have been him skillfully riding the political currents.
Then Covid hit and he took a pretty sharp turn to the right. Again, from a political point of view I can see the savviness. There were always going to be a lot of people who were resistant to letting the virus turn their lives upside down, and he fashioned himself as their champion. And substantively, there were some issues that he was right about, including reopening schools and prioritizing seniors when the vaccine first came out. But IMO he doubled down on his rigid ideology to the point where he went from being "pro-vax, anti-mandate" to functionally anti-vax (appointing a quack surgeon general and de-emphasizing vaccines to the point where, when you went to the State Health Department's website, the first thing you saw on the vaccine section was information about monoclonal antibodies, which is something you take after you've already been infected.)
The thing is, having followed him for the past few years, I know he's not stupid. I think he knows exactly what he's doing, and everything is part of a strategic plan to get him to the White House. And he may well succeed at that.
On the other hand, there are two things that could hold him back. The first, as others have mentioned, is Trump. Maybe he has some secret plan to outmaneuver Trump and get the nomination, but I think it's going to be really hard, mostly because I can envision zero scenarios where Trump graciously concedes the primary and endorses him. Maybe DeSantis beats him so badly he becomes an afterthought. Maybe Trump doesn't run. Maybe by 2024 he's dead or in jail. But in a straight-up matchup, it's going to be very hard for DeSantis to get a clear victory.
The other factor, which I've seen discussed far less, is his personality. The fact is, DeSantis is kind of a weird dude, an introvert without a lot of friends or longtime advisers. There's no Karl Rove or David Axelrod pulling the strings; it's mostly just him and his wife. My brother, who lives in Florida, is very conservative, hates Trump, and voted for DeSantis in '18, so I would figure he'd be a natural supporter. When I asked him about DeSantis, he told me a story about meeting him at a conference a few years ago, when he was first running for Congress, and having a painfully awkward conversation that was only saved by his wife coming over and joining in. I could see that being the kind of thing that comes out over the course of a long primary season, particularly if Trump identifies it as his weakness and zeroes in on it ("Weird Ronnie"?)
