You guys are putting too much emphasis on the clone spam, and Naruto launching a direct assault. Thing is, while that approach has worked before, bull rushing Ruby in a frontal manner is not likely to work so good most of the time. But simply being able to easily destroy the clones is not enough by a big shot, that has always been the case since the very first time Naruto used it. Though they don't always dispel in one shot, I guess it depends on how much chakra is given to them. Most notable example I seem to remember for base Naruto is the thing with Madara's incomplete Susanoo. And Naruto knows how to manage his clones when needed. Just look at the war, he created so many and spread them out to lend help to others.
Like Nico said, the important thing is how he uses them in strategic ways, which is what he has always done and succeeded against opponents that outclass in skill, versatility, normal intelligence etc. Ruby has better speed, but it's not like it's the first time Naruto has been at such a disadvantage, he can adjust his battle plans to compensate. The thing is, Naruto doesn't need to run at her directly while holding a ball of orange energy in his hand. There are other things that could be done.
For example, Naruto could use the smoke clouds that come as a result of him activating the technique or the clones being destroyed to transform into piles of rubble, or direct his clones to do the same. Judging by his fight against Pain, it seemed like he duplicated the rubble, but it's whatever. He can then transform back when Ruby's guard is down and smash...a Rasengan or something into her.
The same applies kunai and shuriken. Once he throws several wind enhanced versions of them, and studies how Ruby handles them, he can work towards exploiting any opening he can find. It's not guaranteed that this will work, since Ruby has lots of options, but it's not like Naruto's anywhere near short on chakra, and Henge is D-Rank anyway. His clones can transform into weapons, and then he can fling them at Ruby. He could also infuse them with wind so they don't get destroyed easily. If she uses something like...fire that counters wind, can't say it would work. But if she tries to deflect them or something similar, the clones can then transform back and catch her off-guard with whatever jutsu. Sort of like what happened with Pain.
Also, Ruby's versatility is cool, but how good is the AoE and how high does the explosion extend? I mean upwards. Bcause Naruto can also use his clones for better maneuverability. They can fling him sideways, upwards etc to get him out of harm's way. He's also good with using his surroundings to either gain an advantage, or avoid or minimize damage, as shown in the hospital rooftop fight with Sasuke. And since Ruby's weaker, he can actually afford to take many of her ranged attacks since they don't ignore durability + Naruto has mostly taken attacks from stronger opponents anyway, and his clones can also act as shields.
And I highly doubt Naruto would be caught napping by her techniques or anything. Not because some of them are common in his verse, but because of the usefulness of his clones in this situation. After his training with Yamato and Kakashi, he has learned how to utilize them better. Just like against Kakuzu, he can send them in small or large numbers to observe Ruby's fighting style, test out her abilities and carefully observe how they work, so he can be better equipped and prepared to handle them. It does not matter in these moments if Ruby takes them out easily, the point is that their knowledge and experiences on how Ruby goes about combat + the effects of her techniques will be transferred to him upon dispelling, allowing him to use more efficient and effective strategies.
Fire would counter Naruto's wind but the same also applies for Ruby's lightning. Naruto and his clones can handle the gravity the same way they did with Pain's, I guess.
And also, the good old toads. Summoning boss Gamabunta will help pretty well if Naruto's having trouble. For starters, it won't be like the Grimm thing because I'm sure Gamabunta scales to at least 500 tons. He can spit oil that can restrict movement, and he also provides a direct counter for Ruby's fire, so he can cancel it out if Ruby wants to overwhelm Naruto's wind, for example. Dunno if Ruby uses earth dust. If so, and if she can use it to make earth based defenses, there's a chance Gamabunta's water wouldn't work. Though it might be a NLF since Ruby's weaker.
Anyhow, Gamabunta can also help counter flight to a limited degree since toads can leap really high, though shinobi can naturally do the same, and Naruto can propel himself with his clones or other buildings and platforms around. Also, it's not like Ruby will hang in the air forever, Naruto can just play possum and wait for her to descend. Gamabunta can also trap targets in his belly somehow and make them confused, but I don't remember how. Same thing applies for Gamakichi + Starch Syrup and combination moves, but he's weaker and I dunno if he can spit oil and trap people in his belly. Also, no counter for Frog Song + Frog Duet....
After everything, I vote for Naruto. But I'm also going to unfollow because I know how RWBY vs Naruto normally is, and I want no part if I can help it. Just want to know:
How strong is Volume 4 and Volume 5 Ruby really? I've seen at least 141 tons, but I've also seen 300 tons. I checked a few profiles some time ago, and I didn't see any calc for 300 tons, so I'm going to believe in 141 tons at the least for now. If 300 tons is based on the characters being much stronger than their pre-timeskip selves, I could also say the 500 ton characters in Part 1 Naruto are now around 1 kiloton because they got significantly stronger, and I'm sure you could do that for a lot of verses.
As for Rasenshuriken, I don't think it should even be restricted. I know it one-shots if it connects, but isn't it like High 7-A Excaliblast? It's not like it's 100% guaranteed to be successfully pulled off. Naruto has to hit with it in relatively close range, something that's going to be pretty hard to pull off without some form of trickery due to Ruby's speed + it also damages him.