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Let's review the issue:
1) Krauss: he won so many loser flags that I can only say: he is a moron, period.
Honestly, he is a total idiot and is probably the main reason why things turn south in Umineko. All Ushiromiya assets (except the gold) are mortgaged. They have nothing and in 1984-5, they could be kicked out anytime.
The only solution for him is when they got the gold, but this part is actually a problem with the culprit (they certainly don't care about the gold, but it is a driving force for the batshit murders)
2) Natsuhi: since Kinzo is in the grave, there is no way for her to have a happy end, unless she finally realize that her delusion is nothing but a mere way to find a "compensation" to her shitty life.
I think the only way to fix that is Jessica, and to some extent Krauss and Eva.
3) Jessica: too much linked to what happen with the stupid inheritence. It would require Krauss and Natsuhi's "good end" for hers with Kanon, heck Kanon needs to go forward for this.
4) Eva: If Krauss can relinquish the title of the "head", which IS possible, it would be fine.
5) hideyoshi: money
6) George: should not be a problem
7) Rudolf: money + a matter related to Battler I assume
8) Kyrie: ditto
9) Rosa: Hard mode. Money + Maria + love. And I cannot see her "genuinely" loving Maria anytime.
10) Maria: everything is about Rosa, and if the "evil witch" is defeated, it is very likely her obsession with magic will be left aside.
11) Shannon: see George
12) Kanon: needs to get past the furniture issue
13) Nanjo: money (?) (for his grand daughter)
14) Genji: not hard
15) Gohda: not hard
16) Kumasawa: hard to say
17) Kinzo: impossible in "reality", but possible if his legacy is honored.
18) Battler: truth about his birth (?)
19) Beatrice: exist without screwing Meta Battler victory condition
20) Meta Battler: proving the culprit is not a witch, but also not "human"... (probably a multi chain of culprits). Must also be the one to defeat Beato
21) Erika: proving the culprit is human
22) Lambda: eternal game => impossible and Episode 5 hints that she actually doesn't mind if she loses
23) Bern: Crushing Beato, converge with Battler's objective, but contradict with the means etc.
And I believe my list is oversimplifying the headlines.
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