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>Why do people ship Ash and Misty
If you weren't there you just don't know. We literally didn't have a chance not to.
In Japan, Kasumi was meant as an Asuka-clone for kids, as part of the post-Evangelion wave (Rei clones are more prevalent around this time, but Asuka clones also popped up. Remember, Eva had JUST aired when Pokemon began).
Kasumi's entire schtick was to be comedic conflict with banter between Ash and Brock, as well as sex appeal (confirmed in interviews). In that respect, she was portrayed as an archetypal tsundere but with incredibly slow development. Her hints were the "childhood friend"/"Expected couple" variety that is common in Japan (ie. If a boy and girl grow up together as friends, its expected that they will be married someday, even if the kids don't know it). This is a cultural cliche of the Japanese that stems from real life social expectations from the Showa era.
Now we come to America. Misty had all the baggage of Kasumi, but handled ever so slightly differently (due to burger writers and consumed by burger audiences). From our frame of reference, the conflict/tease character is a direct Hollywood flag for "inevitable love interest", and she was portrayed as such. Tomboys were really popular in coming of age media at the time as well, it was a slam dunk. 4Kids went above and beyond as treating Misty and Ash as an inevitable couple, both in the show, and with external material (Music/Stage Shows/The movies/Merch/Bumpers/Advertising/Etc). For an entire generation, Misty was the first anime girl that they were exposed to. Little boys fell in love with her, and little girls wanted to be her. Past a certain point, we were all shipping them before we even knew what the fuck that is. The setup is devilish, because her being a tsundere and Ash not pursuing her is an unstoppable force meets an immovable object, and that just compels the audience to root for her even more. Over time, Pokemon became something else, but the feelings live on.
