As far as what I would consider bad personal feelings aside, Faiz. I love Faiz to death but it is a show with flaws. Outside of that though, with personal feelings aside, everything else I've seen I consider pretty good to really damn good, to close to perfect.

Despite it sitting as an anniversary series, you don't have to watch any series prior, as it all takes place in alternate universes rather than the original Riders' universes.
So you can just start it up. And don't worry. It intentionally starts confusing, so even seeing every Heisei series won't stop you from scratching your head at what's going on in the first episode.

Ah makes sense that does.

So what Kamen rider shows have you watched as you have said everything else you has been good.

From beginning to end
Black
Kuuga
Agito
Ryuki
555
Blade
W
Gaim

Started but still need to finish
Hibiki
Kabuto
Den-O

...
...
You finish Den-O now! MAGGOT! :lol
(How do you like Den-O so far? It's literally my favorite Rider series ever! :D)

I liked what I saw of Den-O. I love all of the Imagins, especially Urataros. It was actually the first Rider show I started, but I stopped at the time to watch Zyuranger and ended up watching Ryuki afterwards instead of returning to Den-O. I'll get around to finishing it eventually, I'd just rather finish up Kabuto (a show that I really, really enjoy) and Hibiki (a show that I find utterly interesting) first.

Okay I see what series you have and haven't gotten through now.

For me I consider the second half of the heisei era the weakest section of kamen rider and that seems to be the area you have less explored, of course this is all my opinion on the matter.

Well... what matters is that you enjoyed it. That pleases me. I am seriously thinking about re-watching it. :D
(You know Winston, you seem like a cross between Urataros and Kintaros, with a sprinkle of Momotaros. :lol)

Hibiki is amazing. I'm on Episode 15 of the show and I love every minute of it and I am starting to warm up to Asumu and of course, Hibiki remains awesome. :D
(I do enjoy the Oni/Music theme that this show has!)

On the other hand, I didn't really enjoy Kabuto all that much. It was mostly due to Tendou. He was awesome, yet a jerk. Kind of like Kusaka was. I stopped around the twenties, but I do plan on finishing the show since I do want to see how it ends.

I've seen all of the 90s movies as well.

True, and it's been through personal choice. Everything after Den-O doesn't really grab my interest. I really, really don't like the designs from Kiva, nor the music, and those are factors that add to my being able to get into a show (although I do like Ixa's suit). Decade I honestly just don't know if I want to watch, though I love the first OP and the Decade suit. OOOs is the same as Kiva. Fourze I is one I actually will get around to eventually since it seems like a fun little show. Wizard, same as Kiva and OOOs.

I've said it before and I think what I have completed and listed shows it, but when it comes to toku I do prefer shows that handle the material a bit more seriously. I don't mind humor and comedy, or even if the show is a little kid friendlier than others. But I do prefer it a lot more when the elements of fun and serious are mixed well or it's mostly serious, it's just what I prefer.

I kinda look like Ryotaros when he's possessed by Urataros as well.

I only got three in before I stopped for the time being. I love the environment and how different it is. Though the whole musical number part of episode one threw me for a loop. Kabuto I outright love. I love the action especially and I think it's the best I've ever seen in Rider. And as for Tendou, he's my favorite main rider.

For me, the only Rider shows worse than Faiz are the last 19 episodes of Hibiki (which is essentially distilled Faiz) and sometimes Kiva, depending on my mood. And the only Rider shows I haven't seen from start to finish are the original, Skyrider, Super-1, and Black RX.