I'll use the names Daisuke and Davis to make this easier to understand, Daisuke is the original, Davis is the dub version.
Daisuke is abrasive, in the sense that he can be aggravating, but he is, fundamentally, someone who lacks pride or a sense of self worth, Davis translates this abrasiveness into american high school jerk jock arrogance.
When Daisuke heard he was going to face Ken's championship team, he said it wasn't about winning or losing, it was an honor to get to play against such skilled people, Davis immediately starting bragging about how he'd beat them easily to show off.
Daisuke was mad at Ken for Being the Kaiser because someone with so much ability to help others was using it to hurt them, instead, Davis just thought he was an asshole.
Daisuke NEVER makes possessive statements about Hikari, it is HIS job to impress her, she has no obligation to reciprocate and he never says or implies she does, he never says anything outright that he likes her, everyone knows because he's bad at hiding it, but he is extremely vague about it and never makes any kind of move, the bit you did where a senpai needles him into doing something about it does make sense, Daisuke is extremely deferential to people in higher social positions to himself.
Davis is EXTREMELY possessive and entitled, and states it very clearly and bluntly, and tends to verbally blow off the older kids when they give advice (and then follow it anyway, because the dub can change what characters SAY but not what they DO).
Daisuke has a decent sense of priorities, in that he puts his crush on Hikari to the side when things are serious and won't bring it up if something important is happening (a sub theme of 02 is how romance is a PART of life, but it's not actually that important), Davis will randomly mention it and pick snitfits over it at wildly inappropriate times.
Daisuke’s willing to uplift other people when he thinks they deserve it, and he’s also the kind of person who’s a bit lacking in validation, because he's a bit insecure, and at the start of 02, he seems to have no friends at all other than Hikari. Davis tends to lash out at others and thinks he's the best, and is also probably insecure, but in a different way, the jock way where you need to puff yourself up to feel big.
Daisuke and Takeru were friends decently quickly, Daisuke was concerned over Hikari having this new friend who was chummy with her for seemingly no reason, and it's important to note that Hikari and Takeru are both so closed off that they didn't tell the other three LITERALLY ANYTHING about how they knew each other or their former adventures until the meeting in EPISODE 17, and even then, it was the older kids telling them about it, Hikari and Takeru still said nothing.
More pertinently, we reach our second major obstacle in terms of why Daisuke and Takeru start off on the wrong foot -- Takeru has a very ^^ kind of personality, who deflects things and teases. That is the exact kind of personality Daisuke plays very badly with, because he’s blunt and straightforward and generally tends to be suspicious and defensive when he thinks he’s being made fun of. The dub version just makes this worse, since it makes Davis more obviously possessive.
What else... Daisuke doesn't like flirts. He thinks it's dishonest and insincere, it's why he initially picks a fight with Wallace in the Hurricane Touchdown movie.
Honestly, if you want info on the original dubs character arcs, I'd suggest Shihalyfie on tumblr's character introspective essays, they do a LOT of research into 02's materials to try and translate the extremely subtle character arcs, they supply a lot of citations that can be a fun read, too, like interviews and such.
Links don't work in ao3 comments, but a basic google search of Shihakyfie and any of the 02 kids names should get you to her pages, the one on Daisuke, Takeru and Hikari's weird triangle is really interesting.
Keep in mind, Simon is not Daisuke's senpai. The two of them are in the same year of school. Simon only happens to be a few days older than Daisuke in this context. Daisuke also looks up to Simon due to events explained in Chapter 7, where Simon helped him out against bullies who were harassing him. So, in this context it would be someone whom Daisuke looks up to that gets him to confess his feelings to Hikari, whom at first he assumed didn't hear him due to her fever making her fall asleep.
Senpai isn't just about age or school, it's about seniority, Daisuke joined Simon's dojo, and in that dojo, Simon has seniority as the Senpai even though he's only 3 days older in age, the rules for that are a bit odd.
Also, as I said, Daisuke is just naturally differential, he doesn't think much of himself but thinks the world of other people, someone he thinks is cool encouraging him would be a solid push for that.
Honestly, the one thing that bugged me the most was...
Like.
With the adventure kids, them fracturing apart when Taichi left makes sense, he was a motivating force and they all barely knew each other, and barely got along by that point, too. (I think Mimi and Yamato have still never spoken a word to each other in 25 years.)
The Adventure 99 kids are destined heroes thrown together by fate, they're not a cohesive social group at all. (Contrasting the 02 kids, who absolutely are a social group and hang out all the time even when no Digimon stuff is happening.)
But Daisuke is ALSO a motivating, forward thinking force, and a surprisingly capable one, for all that he can't seem to explain himself at all.
Jou WASN'T, he tried to be a leader people could rely on, but absolutely lacked that vibe, so everything fell apart, but Daisuke doesn't.
Daisuke isn't as good as Jou at preempting issues and anticipating his teams needs, but he is good at getting everyone moving in the same direction, it's WHY he was 'leader' of the 02 kids, who were actually a friend group first and a group of destined heroes second, he got the gaggle of goofballs to focus on the tasks at hand and got them out of their heads to focus on the here and now.
Also, three of these guys are Tamers, who were ALSO a cohesive friend group. (Though Shaochung wasn't overly much part of that, though iirc her and Ruki had a thing?)
The split up arc after losing Taichi was to show the difficulties inherent to just grabbing strangers who don't know each other and trying to force them to become a team, but you've replaced the lot of them with people who DO have and form cohesive mutual bonds, so it shouldn't have been much of a thing, or at least, not the same way.
It's a bit late to do anything about it, and it's not bad or anything, just really confusing.
Keep in mind, that this version of these characters aren't all that familiar to each other. With the exception of Jianliang and Xiaochun who are brother and sister. Ruki only knew Simon due to them meeting prior to the adventure, same with Nia and Daisuke. The split up was more for the fact that despite how Daisuke proved to be an effective substitute, he didn't have all that certainty in himself to keep everyone together. Especially when each of them went off on their own directions to find something. He only left to find food, only for him to get roped into the restaurant. I do understand that it was confusing. If you have any other inquiries about the story, feel free to let me know.
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