I have been trying to get a friend through Kamen rider and it has been taking a while, should I have him skip the more contentious seasons or just try and get through all of it we can?

I say have him skip the more contentious seasons for now and then later on he can go back watch those seasons later.

Yeah, I'd definitely say it's okay to skip over whatever seasons seem least interesting. They'll still be there to get around to later, and if one of them turns out to genuinely be a huge slog to get through, I'd imagine it'd be less frustrating knowing it isn't "preventing" the cooler shows from getting their turn.

This is pretty much the same advice I always give for recommendations, but basically, when it comes to entertainment, following your heart is always the best option. Watching Kamen Rider isn't studying for a test, and there's no "proper" way to do it, so do what you want.

Thanks for the response. This plans makes sense and because I know what he likes and what he does not, given we get through shows at what feels like a slow rate, having him go through a season he might not like might not be the best and just getting to the more agreed on better ones work better.

Who's your favorite composer for Kamen Rider? Shunsuke Kikuchi is still my #1 favorite.

For me that's gotta be Toshihiko Sahashi. There are some individual shows with soundtracks just as great, but I don't think you can top the variety he brings to the table. The eerie atmospheric tracks and heroic guitar shreddage of Kuuga are worlds away from the relaxed and sentimental sound of Den-O, which is itself totally different from Zi-O's epic Egyptian shtick. I think it's pretty telling that for the Rider show about musical demons, he's the composer they went with.

Eiji Kawamura. There is no Rider show with a better overall soundtrack than Black.

Honestly Go Sakabe his work on both Ghost and Zero-One is some of the most energetic and soothing scores in Kamen Rider.

The man, the myth, the legend, Shuhei Naruse. One of the reason Den-O was great was because of his music. Then he gave me the one reason to finish Kiva whether I like it or not.
https://www.youtube.com/watch?v=tXgY7IKXrIA

And let's not forget Cher Watanabe for these two gems.
https://www.youtube.com/watch?v=eDmK2mn3DNc
https://www.youtube.com/watch?v=GmxMS5zg97M

While we're talking composers anyway, I'd also be remiss not to give a shout-out to Koutarou Nakagawa, who worked alongside Shuuhei Naruse on Decade, Double, and Drive's soundtrack, as well as handling OOO and Wizard by himself.

With Naruse doing Fourze's BGM, the two of them together pretty much defined the sound of an entire era of Rider shows, and if you're one of the many people who consider Wizard's music one of its bright spots, or who loves Tsukasa's epic speeches and flamenco-flavored transformations in Decade, or whatever else from any of those shows, you owe one or both of them some thanks.