It is quite hard to narrow down 1 character for each servant class to have in a fic, here is my attempt:
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(Note to self, everyone will have memories of a mix of a BUNCH of timelines)
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Archer: shirou emiya (teenage form)(will be engaged to rin, sakura, medusa, arthuria and medea(not to jack or illya tho. Jack will be an adopted daughter and illya a little sister)). Master: tohsaka rin(fate stay night)
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Berserker: lancelot(fate zero)(i was VERY tempted to use heracles, but his powers would make him VERY hard to write). Master: illyasville von einzbern(fate stay night)
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Rider: medusa(fate stay night). Master: sakura matou(a timeline where "that stuff" never happened. Sakura was adopted by the matou but that's it! She was never taught magecraft and nothing horrible-beyond-words ever happened!)
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Lancer: Diarmuid Ua Duibhne (fate zero)(caster will use her noble phantasm to remove the curse on his mole)master: arthuria pendragon(fate stay night)(yes, one is the master of the other)
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Saber: arthuria pendragon(already explained). master: Diarmuid Ua Duibhne(again, already explained)
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Caster: medea(a version similar to fate stay night, but where she is rescued by shirou instead of Souichiro Kuzuki). Master: jack the ripper(fate apocrypha)(yes, they are each other's master, just like lancer and saber)(medea will be like a mother to jack, and jack in turn her daughter)
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Assassin: jack the ripper (fate apocrypha) (while medea will be like a mom to her and shirou like a dad, all other of the family will be like uncles and aunties to her)master: medea(again,same situation as lancer and saber)
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Name changes(to blend in, everyone decided to share the same last name and be one big family):
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Archer: shirou emiya: archer tohsaka(nickname: shirou)
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Archer's master: rin tohsaka(unchanged)
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Berserker: lancelot: berserker tohsaka
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Berserker's master: illyasville von einzbern: illya tohsaka
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Rider: medusa: rider tohsaka
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Rider's master:matou sakura: tohsaka sakura(a/n: i just remembered japanese names are "family name first" -_- oh well, i am lazy and this is just a rought draft of my ideas, sooooo...)
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Lancer: Diarmuid Ua Duibhne: tohsaka lancer
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Saber: arthuria pendragon: tohsaka saber
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Caster: medea: tohsaka caster
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Assassin: jack the ripper: tohsaka assassin
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Ok, now for the universe integration i was thinking dxd
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Here are the ones who will go to class:
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shirou, rin and sakura will be in issei's year(not sure if all in the same class tho)
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Illya will still be in elementary school, but nearing high school(maybe arround 12 years old while shirou rin and sakura are 16), wile jack will be barely beguining elementary (maybe 6 or 7 years old)
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Medea will be a teacher for jack's school year
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Lancer and saber will have jobs as martial arts instructors in a dojo(saber teaching swordwielding and lancer teaching spearmanship)
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Lancelot and medusa will stay dematerialised when their masters are at school(with lancelot not even showing up in public)
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Comand seals will regenerate 1 per day(like fate grand order(and likewise, 3 comands can be used to revive a killed servand, also the contract won't be broken when all comands are spent)) and the master does not need to give mana to the servant( the servants will be able to regen mana themselves like if they are alive). Comand seals will ONLY be used in dire situations even if they are more "expendable" now, as everyone will still consider them too valuable to use unless absolutely nessessary, and they respect each other enought not to use the seals to comand the other into doing something against their will or for a mere prank