It's unlikely but not impossible that he'll land that properly without Himiko outmaneuvering him as noted in the very argument you quoted a single sentence from, without any context I might add.
I don't think it's unlikely that he'll land a proper grapple on Himiko.
I'll just reply to the points in the main argument rather than just making my own post because that's simpler.
her speed and overall skill advantage is gonna make that grab hard to land especially since in this key Izuku isn't as used to fighting opponents faster than him yet and given the location, Toga can spam her Stealth Mastery something shown to take Deku by surprise in the past to slowly weaken Deku overtime through cutting, stabbing him, sucking his blood out with her machine, etc and well Izuku does have amazing pain tolerance, hes not immune to pain and its gonna slow him down alongside his stamina getting worse as it continues
I don't think that Himiko Toga outskilled Eraser head as shown in the profile
Himiko Toga literally did one dodge. I'm serious. I went back to watch the episode. All Himiko Toga did was flip over Eraserheard while he was using the pully thingy (I don't know what it's called), stab Eraserhead, and dodge then leave. That's not out-skilling. It looks to me to be more of a feat of Acrobatic skill rather than actual close-quarters-combat skill. They didn't have a prolonged fight. Ironically, a few seconds before, Izuku was dodging Himiko Toga while he was suprised from Himiko Toga suddenly changing from Rock Lock to herself. Eraserhead even deduced that Himiko Toga was using Shapeshifting while she was impersonating Rock Lock because of a stab wound that (I think) Eraserhead/Izuku had.
Since this is the scenario where Izuku and Himiko fight instead of (I think) Ochaco and Asui, I went back to see how the duo faired against Himiko.
Assuming that Himiko Toga stays around the same level of skill in Hand-to-Hand Combatant in all of her
U.A Beginnings Saga Keys (That is to say, that she neither improved drastically or worsened drastically), then it could be said that Himiko Toga would be able to beat Ochaco and Tsu without breaking a sweat, since Eraserhead is definitively above his students and she's above him, right?
No. In the video, Himiko gets dodged by an
injured Ochaco, disarmed, and pinned down. Does that mean that Ochaco is suddenly able to out-skill Eraserhead? No. I don't know where the logic came from to put Himiko Toga as "out-skilling" Eraser head, but Himiko Toga only "out-skilled" Eraserhead as much as Ochaco "out-skilled" Himiko Toga.
It doesn't even list that Ochaco did that in her profile.
Skilled Hand-to-Hand Combatant (Has learned the "Gunhead Martial Arts", a fighting style based on grappling and grabbing techniques)
her speed and overall skill advantage is gonna make that grab hard to land especially since in this key Izuku isn't as used to fighting opponents faster than him yet and given the location[...]
Himiko Toga is able to get grabbed by Ochaco, who is far less faster and skilled than her. Sure, a person could argue that Himiko Toga was holding herself back since she knows she is far stronger than Ochaco, but then that leads me to my next point:
We’ve seen how agile and slippery she is, I doubt Deku’s pinning her down unless she throws the fight
Himiko Toga throws the fight.
I'm sure everyone here knows how Himiko acts around Izuku, but I'll give a little summary for anyone that doesn't: Canonically, Himiko Toga is madly in-love with Izuku. Like, Yandere type of love. Of course, by this time she doesn't actually
have feelings for Izuku yet
Himiko develops feelings for Izuku after seeing him badly injured while being carried by
Mezo Shoji during Vanguard Action Squad's attack.
but considering that she'll be cutting him...
Izuku's appearance matched her type of "tattered guys reeking of blood"
And this crush develops fast. Like, within a few seconds fast. I'd bet that if Izuku's actually being beaten down, she'll be developing a crush on him based on how he looks. Himiko Toga went up against Ochaco and Tsu before seeing Izuku, so it is In-Character for her to mess around with her food (See the entire fight scene) Sure, she could spam Stealth Mastery, but at best, she'd only do it like twice because Vanguard Action Squad Himiko Toga only used it as a starting move and then just stayed in close-quarters-combat to fight.
Considering that Himiko Toga would largely be carefree and wouldn't actually use her Eraserhead levels of skill until she is provoked, Izuku pretty much catches her more often than not because Himiko Toga straight up wouldn't be using her speed advantage, as well as not knowing that Izuku can actually pin her down. It literally takes one grab. The chances will only increase as time goes on, especially at the point when Himiko Toga develops feelings for him. Hell, Izuku can even use
Social Influencing on Himiko Toga while she's pinned down if she's actually struggling to get out.
If Izuku is getting pressed enough, he can just destroy the forest area with his
Air Manipulation and then Himiko Toga has to actually face him in close-quarters-combat.
(Unless it's somehow linked to his AP)
I vote for Izuku, count my vote.