If I were to recommend Rider to newbies, I would first put together a list of the Heisei shows and rate them by ease of visual digestion.
Kuuga: Violent, dark and yet wholesome, with some poorly aged CG. Has great characters and lore. A badass with a gas mask and a rifle saves the day. 9/10
Agito: Both better and worse than Kuuga, with amazing battles and characters, but the writing is not as good. 8/10 I wanna marry Ozawa
Ryuki: Battle royale with a literal retard as the MC. Some great characters (including a motherfucker with a snake motif) but the writing sucks hard in the middle. Great beginning and end though. 7/10
Faiz: Amazing characters and action, with a kickass score. The writing is stupid but the suits are great. You will want a Faiz phone near the end. Honestly a guilty pleasure with my favorite secondary rider of all time. 8/10
Blade: Here's the heavy one. Badly acted, and full of nip memes, but the story is superb and the score is phenomenal. Has a kid character though, but she's not terrible. 7.5/10
Hibiki: A quiet, slice of life show centered around a boy growing up into a man, with music as the theme. The first 29 episodes are beyond words, with some of the best writing and plot development. The other 19 episodes, thanks to a production crew replacement, is more action oriented with a shithead fuck secondary main character. Episodes 1-29 = 10/10, 30-38=6/10.
Kabuto: Tons of action, a cocky as fuck main, and another main who is so relatable it hurts. The action is great, and the characters are top tier. The suits are sexy as fuck, and the writing remains solid throughout. 8/10
Den-O: A comedy series with time travel and some of the best character acting. A hot sister and train companion (no, not the loli) helps too. 9/10
Kiva: A more drama focused series that shows two different characters in two different time periods. The love triangle(s) can be a bit much, but the series is critically underrated. 8/10
Decade: DO NOT WATCH UNTIL YOU HAVE SEEN KUUGA THOUGH KIVA...and maybe some showa era stuff, I dunno. A cocky asshole gary stu kicks ass through different dimensions and becomes one of the most likable riders in the franchise. 9/10 but the ending sucks ass.
W: Reddit loves this series, but I am indifferent. Basically, a loser detective and his autistic partner solve crimes along with a dickhead cop and an annoying cunt female character. Good action but overrated. 7/10
OOO (o's): Great characters, good music, a sloggish middle, an absolutely BASED secondary rider, and a 12 year old female villain. Good shit. 8/10
Fourze: a high school focused show, its the most non-offensive and cheerful series with a loveable main character (and a goth best girl). Total lunatic villains and a goofy ass suit. 9/10
Wizard: SEXY suits, amazing action, good story, okay characters, and fucking atrocious pacing. Final villain is a literal serial killer. 6/10
Gaim: Starts off goofy, ends up with so many twists and turns you'd think HBO got a hold of the script. Suits are good and the action is great. 9/10
Drive: Good suits, villains that are shockingly deep, a main female character (not the main rider) that you'll simp over, another female you'll simp over, and a fascinating story. 8/10
Ghost:
Amazons: An edgy as fuck reimagining of the original showa series, the first season is amazing. The second season sucks, and the movie is just okay. Both of the main characters are great (fuck you Chihiro) Season 1=9/10 and Season 2=5/10.
Ex Aid: HELLO GAMERS. Doctor uses video games to kill viruses. Lunatic meme character and a waifu bot are also present. SHITLOAD of movies and extra content. 9/10
Build: Surprisingly dark series with another dickhead main and his meathead lover buddy. Has meme characters but is very solid and one of the best shows in the series. 9/10
Zi-O: DO NOT WATCH UNTIL YOU HAVE SEEN KUUGA THROUGH BUILD. Autistic loner meets a husky voiced waifu and her tough guy friend as they go through time and fight mutant versions of the previous riders, all to prevent the kid from becoming a Thanos level threat in the future. Woz is fucking based. Some shitty writing but gets REALLY good later. 8.5/10
Shinobi: Short at 3 episodes, but great show. Wish it was a real full season. 10/10
Zero One: Unlikable characters, amazing suits and action, retarded as fuck middle due to the coof ruining everything. Main character is a massive hypocrite but the ending is decent. 7/10
Saber: overhated and unfairly picked on, the show has great characters, shitty CG, a story that starts off really rough but gets really goddamn good. Another based king is Yuri. The final form theme kicks tons of ass. *spergout near the end, hence the *. 7/10
Revice: Fighting demons with demons. Started off strong, ended with a whimper due to the writer throwing a fucking tantrum over not being able to write his female main character and her lesbian friend as they stomp the patriarchy. Its the 50th anniversary season and the writer wastes it on his OC being unstoppable and totes amazing. I should stop before I rake in more autistic stickers. Demons Driver is badass and the dad is unironically the best character. 5/10
Black Sun: Reimagining of every Brazilians favorite rider show, Kamen Rider Black. DARK AS FUCK, with modern shit like the George Floyd death and the japs experimenting on people in WWII are present, and the focus sharply shifts from Kotoro, a fantastic character to Aoi, a girl who ends up leading a group of future mass murdering jihadists doctors and philosophers. Would be an easy 10/10 if they didn't change gears, so it gets a 7/10.
Geats: The current series. Great thus far, but might end up shitting the bed, who knows. (I wanna bang Tsurumi)
*Autistic rant: Saber is hated because Zero One fags missed their robo waifu and retarded gorilla secondary riders. Fuck me I hate Aruto, he is so goddamn annoying. "BOOHOO I CAN'T JERK MY SEAMONKEY DICK TO IZU, SO SABER IS TERRIBLE REEEEE"