My ranking of the Kamen Rider stuff I've seen so far

The first Kamen Rider show I watched. Completed. Has good action and humor and also has some more mature elements than I'd expect given its target audience. It also has a lot of great hype moments. Btw due to the target audience, there's some obvious product placement, with the transformation tools looking like toys. Some plot points are also predictable, but that doesn't detract from the enjoyment.

The 4th Kamen Rider show I watched. Completed. It has less plot than some of the other entries I've seen (given how the villain's aims remain unclear until the last few episodes), but in exchange it has good individual episode stories, as well as a generally likeable cast of characters (I especially like Gentaro as a protagonist, but most of the others are also likeable; the only exception is the designated comic relief teacher character, who is pretty unfunny and not all that likeable in general). I also liked the fun vibe this show has, and how it also has some deeper morals and darker moments as well despite that (in general I like shows that have a good balance of both lighthearted and darker moments). And in addition, it had a great finale, especially in comparison to other entries (W's finale wasn't as good for example).
I'm putting it as second on this ranking, though it's a really close second, so that I wasn't sure if maybe I'd put it in first place at first, but I'm keeping W in first place despite its downsides (e.g. the less good ending), due to liking its protagonist duo and detective plots more.

The 2nd Kamen Rider show I watched. Completed. It has a completely different vibe from W, as it's more nuanced than that one: in particular many of the factions presented in the show (the Kougami Foundation, the Greeed including Ankh e.t.c) have motives that can't be put into 'good/evil' boxes. It also tackles the topic of greed and desire in general pretty well. The transformations are also more interesting and varied, but on the other hand the cast of characters (with the exception of Ankh) is less interesting than in W.
P.S. In retrospect, I think I'd perhaps revise my score to 7, but not sure, and besides even the slightest modification to that list entry would push it back to my list updates for no reason.

The 3rd Kamen Rider show I watched. Dropped after the 24th episode. At first, I liked the colorful cast of characters quite a bit. However I found the time-travel theme rather surface-level, as they usually go only a few years back, and this only for the battle (which they thus could do in the present with hardly any difference). The humor also often veers on slapstick territory and thus got samey after a while. And I got the gist of the characters too, so I didn't feel like seeing more of them either. And thus, due to these things, I didn't feel like watching any more and ended up dropping it.
At least the OST was pretty good though.

A very good final episode, certainly way better than W's equivalent.

This was a pretty good action-packed movie. I'm putting it above OOO's one due to recency bias as well as liking the main series more.

This was a pretty good KR movie, and certainly way better than the W one.

This was a better crossover than the W x OOO one, but it also helped me realize that I liked Fourze as of the point when I watched the film (ep.14) more than OOO during its entire run.

These were nice skits, and had lots of Akiko to boot (I rather like her).

This was a nice little Amazon-Fourze crossover special, plus featuring a new Fourze state.

I've only seen the W segments from this one so far - at least these were good.

The W part was good, the rest not so much (especially the OOO part was subpar).

Was quite underwhelming in comparison to the main series plotwise.