Kogasa vs 1F Malignut Eater's Shadow (Labyrinth of Touhou 2 Steam)
Kogasa finally gets her revenge
(Before I get into it, I want to mention that even though I've completed Main Game like 4 times now, I've never seriously attempted to fight the Post-Game bosses at Challenge Level before. I usually use Reisen + Yuyuko to skip over the Enhanced bosses I can and then I fight everything else while massively over-leveled. I figured now's a good time to see for myself whether these bosses are as hard as everyone says...)
Anyway, the Malignut Eater's Shadow is an extremely annoying boss. The actual Eater is ridiculously bulky, despite its absurd speed and evasion. And then there's that summon move that it can throw out. Even if you don't actually kill any of its mooks it can still give its mooks an extra turn. This can lead to scenarios where the enemy side gets to attack 8 separate times in a row. Because of this and the Malignut Eater's chance of throwing out Grass Knot, it's recommended to rely on bulky attackers rather than glass cannons.
It's actually possible to skip this fight by using Yuyuko (the Malignut Eater isn't immune to DTH) but if you want to do it the "fair" way, you'll need to give your primary tank the Guardian Subclass. I don't know if it's ever explained in-game, but that specific subclass has a hidden ability to draw aggro. The success rate isn't 100% but it's better than nothing and Guardian has fantastic passives for tanking anyway.
I went with the SDM synergy since it's a synergy that's very physically bulky. Remilia (who has the better overall stats) got Guardian while Meiling got Strategist (a class that can increase and decrease damage taken while its user is in front). I used Sakuya to increase the level of the Synergy boost. Enchanter was used to turn her handy SPD buff into a light heal. I would have gone with a full SDM party but it was too easy for Flandre and Patchouli to get hit once and die. I instead chose Kogasa for my offense. I didn't even remember that Kogasa is actually most appropriate for this fight, I just chose her to take advantage of the boss' weakness to FIR and TRR.
Whoever you choose for attacking, it's very important that you boost that character's ACC. It can be with the Tome of Accuracy or the Frozen Eyes main equip, but you need it because the boss LOVES dodging attacks. It's kind of annoying if you're not Kogasa, since you basically have to sacrifice damage for accuracy (and most characters need all the extra damage they can get to actually push through this boss' absurd defenses). I had a bunch of extra supports including Wriggle (whose poison is very useful), Hina (whose debuffs can be useful) and Reisen (redundant. I forgot Kogasa could inflict TRR on multiple enemies until this exact run. I would have removed Reisen if this run wasn't successful).
I should stress that you can (and should) skip this fight by using Yuyuko. Even if you can mitigate some of the randomness with Guardian, and by setting up early defensive buffs and debuffs, it's not a very fun (or interesting) fight, just a whole lot of RNG.
Music is Kogasa's theme from Touhou 17.5
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