Jobless Reincarnation's 2nd season (episode 13+) is extremely strong, one of the strongest sets of episodes I've seen in a while.
I'm very split on this anime. The high sexual content (especially the deviancy of the main character) is going to make this a very tough watch for many people. Rudy crosses lines well beyond "appropriate". But once you reach ~episode 13 or so, it feels like the story's main plot finally begins and the grand adventure plays out in a very well written way. I just don't think that the typical person will make it that far given how much of a degenerate the main character is for the first 12 episodes.
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For those "deeper" into anime and who have seen a large number of Isekais, I can confirm that this is absolutely "the progenitor". There are so many powers, jokes, and plotpoints that have been stolen (and rewritten) from Jobless Reincarnation into other shows. Its absolutely nuts how many shows I can think of that have taken elements of Jobless Reincarnation's setting. I think if you're "really" into anime, its worth a watch if you're willing to put up with Rudy (the main character).
The pacing of the arcs is good. Knowing that each arc covers ~2 years of Rudy's life consistently gives this a slow-and-steady pace that few other shows can match. While other shows have long-time periods, Jobless Reincarnation really digs in deep into Rudy as a 3-year old, 5-year-old, 8-year old, 10-year-old, 11-year-old and ... (well, that's how far I got so far). Its very impressive for a story to be written to cover each part of this guy's life in such detail.
Now that I've seen this much of the show, I'm pretty sure that they're trying to compare/contrast how Rudy grows up as a person. Even Rudy's dad (Paul) is only like 22 at the start of the show, and now that Paul is 30 you're seeing a great many changes to his character. Its not just Rudy who is growing up here, but the whole cast. From this perspective, the womanizing asshole early episodes for both Rudy (and Paul) are more of a starting point for both characters. Its still a tough watch though and I don't blame anyone if they want to give it up because of what happens in season 1.
Yeah, there's a lot of years between event, since he start in this world from the beginning, it's not like in a lot of other isekai where everything take place in less than 2 years.
I do think that most reincarnation shows cover a lot of time. What's different here is the amount of depth Jobless Reincarnation gives to each timeskip. 4 or 5 episodes per ~2 year time skip is impressive.
Will from Faraway Paladin has basically baby to ~15ish in about 5 episodes. And its a spectacular journey and smooth.
Kumoko from "So now I'm a Spider, So What?" has... actually I like her story and its spoilers to talk about the timeline, lol. But the first season covers ~15 years by my estimate.