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I remember back in 2011 I was skimming /co/ and saw a thread mentioning Gokaiger before it started and thought "oh shit that's cool" and when I watched it, yeah it was cool. That's all it took personally.
My best advice would be to either just start with the most recent Kamen Rider or Super Sentai and catch up to where it's currently airing (which would be easier for Super Sentai, there's only about 10 episodes or so out at the moment) or to look at the history of them and see which shows interest you and just give it a shot. Other than that, if you grew up on Power Rangers it might be neat to check out the show your favorite season was based on (for example, the original MMPR was Zyuranger and In Space was Megaranger.)
If you have any specific interests, for example video games, phantom thieves, trains, time travel, samurai, space, etc. those can also be good jumping off points to find a show centered on that theme.
