I noticed quite a bit more stuff in my second viewing and still yet more things the third time around. This is a busy movie and there is much in it that is easy to miss. Although the movie does not have the same novelty that it first did, the extra details I noticed seem to make the story feel more coherent and less like it has plot holes. I still think that there are plot holes, but I get a better sense of what the director was shooting for.
In addition, problems are a little easier to ignore on the second and third viewing. The personalities of Luke Skywalker and Admiral Holdo come across as more understandable, and in particular the acting by Mark Hamill seems more nuanced.
This feels like this is the least rewatchable of the Star Wars movies, since all of the other movies I have watched repeatedly and still enjoy them. For Star Wars: The Last Jedi, three times seems like enough.