I absolutely recommend it! Slope's Game Room has an excellent, 2 hour retrospective you can put on while you work if you want a pretty good deep dive. Other than that, I recommend getting yourself set with some emulators so you can kind of dig through the series. A lot of the early games are difficult and I think it's perfectly fine to kind of just pick through them a bit, get a taste, move on, return to the ones you like, etc.
You can absolutely feel the arc of design elements through the early series up to the pinnacle, Rondo of Blood. That's because it was all being done by Konami teams, often who knew eachother or were handing the projects off. Rondo hits this sweet spot where you can feel the inspiration of old vampire novels combined with dramatic stage plays (the stages have dynamic names like Feast of Flames instead of just area descriptors), told with 80's anime cutscenes, wrapped into a videogame package. It's truly a work of art that both wears its influences on its sleeve and also that couldn't really exist the way that it does in any other medium. So where do you even go from there? Symphony of the Night! It takes everything that works about Rondo and kicks it to 11 while flipping the franchise on its head with an absolutely rocking soundtrack and sprawling castle. You can enjoy these games in a vacuum, sure. But playing the series up to that point gives you a real appreciation for what they were going for and how they accomplished it. I don't even think you really need to play them in order because going back and returning to previous entries almost feels like fitting in missing pieces of a puzzle.
The series flounders a bit when it hits 3D, but it will always have a special place in my heart. Koji Igarashi takes the Symphony of the Night formula and basically owns the handheld world, especially from Aria of Sorrow into the DS trilogy, A++. Ultimately I think he developed that formula enough on his own that breaking it off into the Bloodstained series feels right and good, I think he's better off this way not weighed down by Konami and the Castlevania franchise, but in this way, we still feel that arc of development. Bloodstained: Ritual of the Night actually took a bit to grow on me, but once it did, I saw it as the most Igavania game that ever existed, he has refined the formula.
All this to say that we just don't get experiences like this anymore, where series have the proper time to cook and develop. Instead we get Concord where they pour millions into something and try and ram it down your throat, "You WILL enjoy this new franchise. You WILL pick one of these characters as your favorite to get invested in, even though we've given you no reason. You WILL make this your ONE game you play because ........ reasons?" Ditto Marathon. Ditto MindsEye (likely). Ditto all the other rubbish they keep pushing out.
EDIT: OH MY GOD! And the Castlevania DLC for Vampire Survivors, how could I even forget. It's been a Castlevania wasteland for years and that DLC is some of the best I ever played. Completely the Richter scenario and getting to the end of it legit made me cry, it was such a love letter to fans and felt like a huge emotional, respectful sendoff for the series that Konami will never give us It's so good, if you're a Castlevania fan you should absolutely play it and if not, save it til the end because it's incredible and bittersweet.
