Correction, Black would be paired with Maskman unless you mean RX, which is befitting since both aired in 1987 and have bittersweet endings. :lolol
As for my pick, it would be Gekiranger and Den-O. Just imagine the five imagins, Momo, Ura, Kin, Ryu, and Sieg, each possess a ranger who is the same color. Ryu Geki Violet and Sieg Geki Chopper would be hilarious. :lolol

The thing about that is that Black did start airing in 1987... but on October 1987; all the way to October 1988. Meaning for the majority of its run it did in fact air with Liveman!

And true, the original SHT's pair-up of Black and Maskman doesn't seem to agree with me on that... but hell with it, Black and Liveman is way too perfect! I'm running with it for this imaginary scenario :p

Fair enough. :lolol
Actually that does work out since it started in fall like recent rider shows.

Who sees Calibur Sophia wear something similar to Warrior Zelda in the future? But if Sophia doesn't remain Calibur, which gender would you have take up Kurayami? Male, female or non-binary like Naki?

How weird is it that Kamen Rider Grease's Twin Breaker is voiced by the same voice actor who did Rey Kivat and Arc Kivat. They went deep with the Kiva throwbacks.

Oh, they really were! I can't really pull up the pic, but it was the pic of the riders pulling out their belts, and Kohei was holding the Sclash Driver like he was holding Kivat the 2nd. I believe he lost a bet in that one, so he had to pull out the driver like how he did Kivat.

Norio Freakin' Wakamoto. In 1998 he appeared in Gingaman to answer the million dollar question, what if Zordon was a talking tree. :lolol

Would you all see a new male, female or non-binary character take up Kurayami as the new Kamen Rider Calibur in Sophia’s place? And how would you see this character brought to life in the hero/heroine route?

You've been asking that same question every day for the last three days, the last time just three posts above this one. I get that you're very passionate about Saber, but you need to understand, it's ok if people don't respond to your questions, especially one's You've been asking over and over again for months. Instead of thinking "I've already asked this question 9 times, maybe the 10th someone will answer", try and change to thinking "I've asked this question 9 times and no one's answered. I guess people aren't interested. That's disappointing, but I know I can't force people to reply to me". It's been pointed out to you quite a few times that people are getting tired of you asking these questions about Saber over and over again. Maybe this isn't the place for you to try and get engagement with your ideas. Have you considered making a blog? Tumblr, for example, has a great system of sending questions to people and reply to other people posts

I just don't have a strong opinion about who, if anyone, uses Calibur at this point.