In fairness, I'll be doing the meme previously posted, plus the Angelwing variant that declumps the numbers a little bit.
Our ten fictional characters, alphabetized to randomize a bit more, are:
1. Ann "Little Orphan Annie" Warbucks from "Little Orphan Annie."
2. Draco Malfoy from "Harry Potter and the Seven-Book Series."
3. Jennifer "She-Hulk" Walters from the Marvel Universe.
4. Kenzo Tenma, M.D. from "Monster."
5. Khlit "the Wolf" of the Curved Saber from the Cossack stories by Harold Lamb.
6. Mary Batson "Mary Marvel" Bromfield from the DC Universe.
7. Masashi "Yuna Kurimi" Rando from "Pretty Face."
8. Reiko "Zombie Shop" Himezono from "Reiko the Zombie Shop."
9. Setsuna "Sailor Pluto" Meiou from "Bishoujo Senshi Sailor Moon."
10. Yuugi "King of Games" Mutou from "Yu-Gi-Oh!"
1. Divide the list up by even and odd. Which group of five would make a better Five Man Band (like a Power Rangers team)? Who would you slot in each position: Leader, Lancer (second-in-command), Big Guy, Smart Guy, The Chick? If you think the team would be improved by swapping one character between the even and odd groups, which ones would you switch?
Evens: Draco (the Chick), Kenzo (Leader), Mary(Big Guy), Reiko (Lancer) and Yuugi (Smart Guy).
Odds: Annie (Smart Guy), Jennifer (Big Guy), Khlit (Leader), Masashi (the Chick, just to be really mean) and Setsuna (Lancer). Khlit's not going to be happy with this team, three women and a really effeminate boy in a skirt. I'd probably switch him with Kenzo to make Team Even better.
2. Gender-swap 5, 8 & 10. Which character would have the most change in their story arc? Which the least? Would any of these characters have to have a complete personality change to be believable as the opposite sex?
Khlit, Reiko and Yuugi. Whoo. Khlit's entire career goes bye-bye, since they sure as _____ did not let women be Cossack warriors in the 16th Century. Let alone become Koshevoi Ataman, or Kha Khan of the Tatars. I can imagine female Khlit as a tougher than nails Cossack grandmother who rules her warrior relatives with an iron hand. Khlit's distrust of women presumably would be lessened by being one of them.
Reiko's character doesn't change too much, being somewhat callous and mercenary works for a male zombie master as well. He might get a little more respect from the police and clients. On the other hand, her twin Riruka becomes a fraternal rather than identical twin. And male Reiko might find the story set in an all-girls school in Germany a bit more exciting/annoying.
Oh, wait. I forgot the bit where Reiko's head is cut off and later attached to a completely different girl's body. Okay, at that point male Reiko's life gets weird(er), as he becomes female from the neck down. (As opposed to Masashi, who appears to be female from the neck up.)
Yuugi: The personality doesn't need to change drastically; a short, underdeveloped girl can be just as good at games and as desirous of friendship. Relationships go a bit differently, though. Anzu becomes the best buddy (which also gives Anzu an actual female friend, something she lacked in canon), while Jonouchi and Honda take on more UST roles as Yuugi's protectors/mostly platonic friends. A lot of the enemies would be even less pleased that this slip of a girl is beating them. Watch Kaiba turn even more interesting colors!
And then there's the other Yuugi, who is still male. He won't realize it at first, only having female Yuugi's memories, but will still come across as kind of butch when controlling Yuugi's body. As it becomes clearer they're separate personalities, and "other Yuugi" is male, things may well get a little sticky in the head.
Angelwing variant: 2, 8 & 10.
That swaps in Draco. Personality barely changes at all, as Draco becomes her parents' spoiled, bigoted little princess. The rivalry probably shifts somewhat from Harry himself to female Draco taking on Hermione as her personal nemesis. Crabbe and Goyle probably become more protective than obedient. Fanfic writers ship female Draco with Harry even more. No substantial changes to the story arc.
3. Compare the matchups of 5 & 8 and 2 & 9. (Ignore canon sexual preferences for the moment.) Which couple would be more compatible? Which couple would be more plausible to people from either principal's home culture?
Khlit and Reiko, Draco and Setsuna.
The first one is highly implausible, as Khlit is past retirement age and Reiko's a high-schooler--plus, Khlit is so far as can be determined celibate. They'd be traveling companions for a short while at most, especially when their religious differences come to the fore. (Khlit's Russian Orthodox, while Reiko gets her powers from Satan. Literally.)
The other pairing looks a bit more likely, especially if it's post-Book Seven Draco. True, Setsuna is slightly older-looking, but not so much as to freak people out, and Draco can probably justify a magical woman as more or less like a witch. The Wizarding world doesn't give a fig about skin color or ethnicity, so that wouldn't be a problem either. On the other hand, Setsuna would quickly tire of Draco's vanity and pettiness--short-term relationship at most, while she's lonely.
Angelwing variant: 1+8, 5+9.
Annie and Reiko, Khlit and Setsuna.
Annie's a prepubescent child. No. The other one's slightly more plausible, especially if Setsuna lets Khlit know she's older than she looks. It'd look freaky in modern Japan, but the two of them riding across the steppes together would excite little comment.
4. Your team is 3, 4 & 6. The mission consists of a social challenge, a mental challenge and a physical challenge. Which team member do you assign to each challenge?
Jennifer, Kenzo and Mary. We'll give brain surgeon Kenzo the mental challenge, sweet Mary the social challenge and super-strong Jennifer the physical challenge.
Angelwing variant: 3, 4 & 9.
Jennifer, Kenzo and Setsuna. Jennifer takes physical again, but Kenzo handles social and Setsuna the mental challenge.
5. 7 becomes 5's boss for a week in some plausible fashion. How's their working relationship?
Masashi becomes Khlit's boss. Khlit, once he finds out Masashi is actually a boy, will cordially ignore any and all orders in favor of his own plan. He was going to do the same thing when he thought Masashi was a girl, actually.
Angelwing variant: 7 and 1.
Masashi becomes Annie's boss. Much more plausible, and Masashi is less likely to blow his Yuna identity. Annie works hard and has good sense, so this probably works out okay.
6. 1 finds him/her/itself inserted into 6's continuity. As far as anyone other than 1 or 6 is concerned, they've always been there. What role would 1 be presumed to have had in 6's story, and could they fit in without going wonky?
Annie in Mary's story. Annie becomes a plucky orphan girl adopted by someone the Bromfields know socially. The quite open superpowers will be a bit of a change for Annie, whose world tends to hide such things, but I think the two girls will hit it off.
Angelwing variant: 2 & 6.
Draco in Mary's story. Draco becomes the stuck-up and bigoted son of a family the Bromfields know socially, and a minor supervillain. Draco would be appalled at having to deal with Muggles pretty much constantly and look for a magical community to join.]
7. 3 and 7 get three wishes. The catch is that they have to agree on all three wishes before they get the benefits of any of them. What three wishes would they make?
Jennifer and Masashi. The latter would probably blow his wishes solo, but this time he's working with a lawyer. So: 1. Yuna is restored to her family, so Masashi doesn't have to impersonate her any more. 2. Masashi is restored to his normal male appearance. 3. Jennifer can never have her ability to switch forms at will interfered with again.
Angelwing variant: 3 & 5.
Jennifer and Khlit. A distinct clash of personalities, but Khlit believes in doing things for himself, so will in the end ask for nothing. Thus the wishes will be: 1. Jennifer can never have her ability to switch forms at will interfered with again. 2. A place where her cousin Bruce can be happy that won't blow up. 3. For her friends to have better luck with love.
8. 6 and 3 are brainwashed by a one-time artifact that works even on people immune to mind control to attack and kill 1. They keep their normal personality, skills and competence level, except any Code vs. Killing has been turned off. Can 1 survive? How?
Mary and Jennifer versus Annie. Plucky just doesn't cut it. Annie's dead and Mary will feel really horrible afterwards.
Angelwing variant: 1 and 2 versus 4.
Annie and Draco versus Kenzo. Annie's a near-genius at accomplishing any task she sets her mind to, and Draco has magic, including the Killing Curse. Meanwhile, Kenzo still has trouble breaking his Hippocratic Oath. He'd lead them a merry chase, but in the end he isn't going to make it.
9. 1, 6, 7 & 9 must help an orphanage full of small and depressed children have a merry Christmas. Who does what, knowing that at the very least the kids will be expecting a visit from Santa?
Annie, Mary, Masashi and Setsuna. Annie has "orphan" in her title, so she knows what it's like. Mary's extremely good-hearted, and the other two aren't bad people, so they'll pull together. Setsuna, as the tallest, gets to play Santa. It'll go pretty well. Mary can decorate at the speed of Zephyr, and Setsuna knows where to get presents.
Angelwing variant: 6,7,9 & 10
Mary, Masashi, Setsuna and Yuugi. The main difference will be less inspirational speeches about pluck and determination, and more card games.
10. 3 and 10 are challenged to circumnavigate the Earth in eighty days or less, using only forms of transportation invented before 1900. Can they do it, or will they be fatally distracted by sidequests or their own personality conflicts?
Jennifer and Yuugi. While Yuugi's duels seem to take a long time, they're actually quite short objectively, so won't slow the team up too much. Jennifer's going to have to take care of all the practical matters though.
Angelwing variant: 3 & 8.
Jennifer and Reiko. These two are much more likely to have personality clashes, and Reiko's habit of raising the unquiet dead to deal with problems will deeply unsettle Jennifer. Expect quite a few more delays.