Speculations I dont feel like we're gonna lose

That chapter title is a red flag right? Are they about to get their asses kicked?
If OP ends after 15 years and goes into a predictable hints then the alliance will lose because of that "red flag"...

But OP will end "in 5 years" and taking it as a red flag is very predictable... So I doubt... If any, I consider it as a "red herring"...
I don't believe this raid should fail.
Luffy surpassed the biggest obstacle of having scrub level CoA and being unable to damage Kaido, leapfrogging it to having the best CoA on the island including the Yonko.
Also this time he will actually use future sight somewhat after all the focus on it when training rather than blind rage preventing it's usage.

Jew D. Boy

Tasteful Crucifix Party
Here’s my problem with the current situation - yes, it really seems like we’re trending towards the alliance getting their asses beat, and by all rights, they SHOULD suffer a massive defeat against two Yonkos and their crews. Even with all their powers combined, it reasonably shouldn’t be so easy to beat Kaido and Linlin simultaneously.

Where I personally get tripped up is the introduction of the New Onigashima Project a little while ago. Kaido said that the citizens of the Flower Capital are unwittingly experiencing their last night of freedom; Orochi is dead or otherwise incapacitated, so once the dawn breaks, the WSC expects to take charge and subjugate all of Wano. With the raid, it’s do or die for the Straw Hats, the Scabbards, the Supernovae, and all the displaced samurai...if they fail to win tonight, they either won’t live to see tomorrow, or won’t reach a new day as a free person.

We’re stuck in a weird stasis where the alliance shouldn’t really be able to pull off the victory here, but if they don’t, the story takes an unimaginably dark turn. How are Luffy and friends gonna successfully execute a second raid if the first one fails? The element of surprise only works once; Kaido will throw whoever’s alive into a cell like he already has with our main character as well as Kid, and the rest will either be killed in their weakened state or otherwise coerced to join his crew. There’s really only one way out of what we’re seeing in this arc, and that’s through.

Oda clearly wants to wrap everything up, which is another reason to believe there won’t be future attempts to get this right. Luffy and everybody else are gonna have to win this time, or it’s curtains for everyone. The tempting fate trope is real, but perhaps this is one of the few times it’ll be subverted by necessity.