IIRC in one episode of the old Girls in Trouble podcast, Lynxara recounted the tale of an acquaintance of hers who works for Crunchyroll and did suggest Kamen Rider to their show-buying people. They thought it was a great idea and contacted Toei about licensing the then-current series. The sticking point was the amount Toei wanted to sell the rights for. It wasn't a batshit insane figure, but the amount they wanted for Rider was at the level Crunchyroll typically only pays for a guaranteed mega-hit anime. While Rider is an extremely profitable show in Japan, the series would have needed to get massive viewing figures on the Crunchyroll site, or else they would have lost money on the deal. In the end they just weren't convinced that Rider could do it.Wow, maybe they will start streaming Kamen Rider and Sentai next.