If a crossover between Sailor Moon 90's anime and Sailor moon Manga/Crystal (post Stars) were to ever happen, how you think the characters would interact with their doubles and what would you like to see happen?
It really doesn't to me. There just aren't that many differences between the two series to really justify alternate realities. Crystal Tokyo and present day work because of the big time gap and age gap, changes in role that Usagi has as queen versus a Sailor Senshi.
If I were forced to do anything of the sort, it'd be something akin Another Story where the present day senshi travel to the silver millennium somehow (Pluto?), yet I'd still rather keep in within one continuity and not mix two.
I also think that picture posted is problematic but thats not OP's fault.
I can see it being like Turtles Forever, with the 90's anime versions being flattened into complete caricatures and the manga/Crystal versions fleshed out since it would be from their POV. All of the 90's Inners would fire off weak attacks to let 90's Sailor Moon beat the bad guy, only for the manga versions of the characters comment how limited and one-dimensional they are. Specific character notes follow:
Manga Sailor Moon would ask her 90's self how she managed to stay so carefree in spite of all she has been through. Anime Sailor Moon would retort that she would be her own kind of Sailor Moon. However anime Sailor Moon would be jealous that her manga self is so much more mature and wonder if Tuxedo Mask would fall for her.
At the same time, manga Tuxedo Mask would get along with his 90's counterpart at first, until they get into battle, where 90's Tuxedo Mask would be shown to have next to no battle skill whatstoever, throwing a rose then standing to the side. For added affect, this would be against a manga style-minion, so the rose would bounce off with no effect, and manga Tux would wonder how his counterpart never developed skills of his own and let the girls do all the work. Anime Tux's lack of connection to the Shitennou might also cause some differences of opinion.
Both Sailor Mercuries would get along great, although manga Mercury would be disappointed in 90's anime's lack of confidence, and the 90's version would note the lack of heart (from her perspective) her manga double.
I can see Crystal Sailor Mars look at her old anime self in disgust. By contrast, 90's Sailor Mars would look up to her manga counterpart, thinking them so much "alike" (and being horribly wrong).
Crystal Sailor Jupiter would wonder how her old self was so boy-crazy, but both would get along fine.
Both Sailor Venuses would get along fine, both showing their serious and silly sides to each other.
im not kidding. There are differences, but the plots all tend to play out the same way in the end save for minor differences (Pluto’s sacrifice, Serenity defeating Beryl, Black Moon’s largely the same). There are character differences too, but aside from Reí the main cast is largely the same too and the comments that speak of the art style being the most notable change between them speak volumes.
For example, I think that if Crystal shared the same plot with PGSM that it’d be a much better option:
*Chibiusa doesn’t exist in PGSM, so adding Usagi and Mamoru’s daughter in and playing off Sailor Luna would be interesting
*Princess Serenity from PGSM is much different than Classic’s or Crystal so the interaction between both and/or the characters could bring something new
*Saturn, Neptune, Pluto and Uranus haven’t been in that world so they’d bring something fresh to it
*Venus from PGSM either working with the Outer Senshi (as she shares qualities of theirs) and being shocked at how carefree and reckless Venus from the manga/classic anime is would be hilarious
There are differences, but the plots all tend to play out the same way in the end save for minor differences (Pluto’s sacrifice, Serenity defeating Beryl, Black Moon’s largely the same). There are character differences too, but aside from Reí the main cast is largely the same
I disagree there's a lot of plotlines one can use due to the differences between the characters
Ami in the manga is somewhat aromatic and antisocial, but her anime counterpart social and open to romance in one episode she confesses to Shingo, who has a crush on her, an interest in marriage and children. Has a few friends outside of the Guardians, Ryo, Kunitachi the park's caretaker, from episode 15, and Natsumi the widow who Ami help fixed up her car. Anime!Ami is also Not So Above It All as tv tropes would say and is a bit pervert (the scene where, when they see Seiya wearing only a towel, and Chibi-Chibi is pulling on the towel trying to take it off she can be seen peeking through her hands.
Minako in the anime never ended up killing up her love interest and as such she doesn't believe she's cursed to never find love also she's is just as ditzy as Usagi if not more so.
And there also Sailor Uranus and Neptune who in the anime at first weren't very nice to anyone.