Okay, so I'm confused about some things. What elemental attacks has Hiei resisted before? I can't just say he has resistance to all the elements possible so I'll go with the ones he has displayed resistance to. He doesn't necessarily have to attack it with Rasenshuriken in the first place. Also, it's not entirely made up of wind. There's still a big ball of chakra there. Did Hiei completely no-sell the spatial cutting? Just because someone has faced something before, doesn't necessarily mean it wouldn't have any significance or effect on him. Unorthodox strategies can come in different forms. You can't honestly say because Hiei is Yusuke's biggest rival and Yusuke has a unorthodox style of fighting, he wouldn't have any trouble with people that use that style of fighting. For example, because Pain got caught off-guard by Naruto throwing smoke bombs and blinding him leading him to be subsequently subjected to Frog Song doesn't mean someone throwing smoke bombs at him wouldn't have any luck doing anything to him. Or because he got clowned by Naruto transforming into his Rasenshuriken only to transform back and slam a Rasengan into him means he won't be affected by anyone using that on him again. Or that because Gai specializes in taijutsu and Kakashi is his biggest rival and they regularly spar with and have contests with each other, someone specializing in taijutsu wouldn't really bother Kakashi. Or let's say, Yamamoto from Bleach has been a captain for years, and has fought against people specializing in Kido or use Kido in different ways, anyone using Kido wouldn't bother him. It simply depends on the circumstances and the opponent involved. I can easily say because Sasuke is Naruto's biggest rival and regularly tanks his Katons which he specializes in and comes up with several ways to deal with them, using his surroundings, location or clones to minimize the damage or straight up evade them without any issues, Hiei's attacks won't be of any problem to him.
I don't even know what I did here, so I'm sorry. I don't know YYH so I have no idea of what Chapter Black is. I'm just going by what's on his profile. Naruto's clones are all Country level. They all have the same AP as him. Back when he just unlocked KCM, they were fighting against and injured people on his level despite the fact that they have limited chakra and durability. And did those demons bother to coordinate their attacks and use their numbers to their advantage? Or did they have the versatility like Naruto and his clones do?
How does it not matter how many? We're assuming that Naruto can create only 1000 clones when he could do that as a kid. Assuming that he can create just 1000 is a very massive lowball. He created enough clones to fill up Kaguya's dimension and referred to it as his personal dimension in that instant. If I remember correctly, Kaguya had to move to another dimension or something to get away from them because of their sheer number. So taking care of 77 or 100 guys casually does not really matter especially if they didn't do the things I inquired of earlier. Just one of his clones was able to hold out against her for some time, despite the fact that she's above him and Sasuke combined, and is superior to Hamura and Hagoromo, who is in turn stronger than Naruto. And he has noticeably better chakra control now, as he's able to casually form a Rasenshuriken and redirect it which he couldn't do even in his strongest forms prior to the timeskip. So, he wouldn't have any problems creating any amount he wants, especially as he has Kurama to continually gather chakra for him. I've seen people mentioning range as an advantage even for people who specialize in or prefer to fight in close range. And Naruto does fight from range, so it's a valid point. Things like Sexy no Jutsu (harem version) might possibly create an opening for him. Or bullrushing him with clones and attacking from underground like he did against Toneri, Replacement Jutsu to evade Hiei's attacks, transforming himself or his clones into inanimate objects using Henge for surprise attacks, utilizing fake explosive tags like I said earlier, or incapacitating him with ninja wire that restrict the flow of energy. Remember like Gemmy said, he created a massive Rasengan for Boruto when being restrained, having gone through a battle against Momoshiki and having his chakra drained prior to that. In his peak form, he and his clones would be capable of doing that, and to a better extent. And they outnumber his dragons by a very large margin (look at what I said about his clone party against Kaguya and him having better control over his chakra to prevent wastage) so I see no problem in that area too. Also, the flight and continuous advice from Kurama.
But hey, I guess we can agree to disagree.