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This man just stole my whole flowDude he does resist Power Null in the Key that he's in which is Apocalypse AnswerArms with his previous Key (True DxD) states the following "All previous abilities, Resistance to Power Nullification (Rizevim and Apophis couldn't nullify his abilities as a result of him possessing Ophis' power of infinity [27] [28])"
Means Divide and Dress Break are usable against Haruka which means that he can strip her of her clothing and constantly halve her and the Summon's AP adding it to his own (as he can interact with spirits). His Limited Durability Negation and Limited Resistance Negation is layered enough to injure somebody with resistance to both still.
Also, how exactly does Haruka's seal work because it says that she can make Ice Coffins and then seal things inside of them would this prevent somebody who can make portals from teleporting outside of the ice coffin? And seeing as Ice Coffin is magic and Issei has resistance to magic I doubt that they'd be effective on him. Plus how will she deal with his Attack Reflection and his ability to grope a booba to absorb energy from the booba to power his attacks?
Pailingal gives him the advantage in combat because it is not like she can tell her booba to stop talking meaning that she probably would even know that they are telling him her attack strategy. Issei himself is pretty smart and can think of plans to defeat more skilled opponents after seeing their powers being used, running away to plan an attack isn't out of character for him either. Couples with his range advantage she isn't getting close to him unless he wants her too.
Also in this key, all of his resistances and abilities are vastly enhanced plus he can manifest both Ddraig and Ryuuteimaru to fight alongside him. Ddraig himself shares most of the same resistances and abilities as Issei and can also summon other dragons to aid him in battle meaning that her six summons will be mogged.
Yu doesn't even have booba to use any of Issei's female-only (i.e. Dress Break and Pailingal) abilities on and I am not an expert in DxD to be copied