It's good dw
Tbh I think Ken is going to be taking this seriously from the get go, if he can't precog or gleam info from Cloud's aura he'll probably take that as a sign that his foe is super powerful lol.
Pretty much. Ken never took chances from what I recall (sorry, only watched the HnK anime long ago... good stuff, man), and even against opponents he was merciful towards he still had many ways to disable and defeat them even without killing them. Being unable to analyze the opponent would just change the "hmm, he's strong, better not take any risks" to "hmm, I can't read him, better not take any risks".
Skill wise I'm pretty sure Ken blows Cloud out the water here, never mind the life long practise of his martial arts but iirc Ken can copy and perfectly use the arts of his slain comrades who themselves have their own skill feats.
That's unquestionable, to be honest. Even without factoring the skill and technique added up from his fallen comrades, Ken is on another league thanks to his extensive training and years of combat, compared to Cloud's much more limited experience and the fact he's self-taught, basing himself only on his natural talent to work around.
I'd say Cloud should have experience against martial artists, but I don't think he's fought Tifa.
Somewhat, he's fought and beaten the Turks who include two martial arts experts in the form of Reno and Rude, as well as Yuffie a professional ninja, but none of them are on the level of someone like Ken. In Advent Children he also defeated Loz who easily beat Tifa, but that doesn't count for Cloud's key for this fight (my bad for referencing Advent Children before)
I think it's skill and experience that gives Ken the edge here, where he should probably trump Cloud in hand-to-hand combat at least in that aspect. I agree, Cloud has a shot here, but I do think I see outcomes where Ken is capable of snagging a victory by just striking where it's right, that and Ken's a man of opportunity when it arises, him aiming to end fights as quickly as possible, especially when he has the edge.
Albeit with high difficulty, I've already voted Ken, but Cloud isn't helpless, however Ken should have the skill, experience, technique, and AP to at least land a finishing strike that of which he usually does.
To be fair, I fully agree on this as well, not so much that Ken can pull a win as much as Ken would pretty much win hands down if this ends up as a close range fight.
I did mention Cloud had a close range option with the Status Effect Elemental Blade combo, but thinking more about it that's not really viable against Ken. Unlike, Ken who just needs a touch, Cloud needs to inflict damage even if a little, it
does if it's blocked but it's not so likely happen as Kenshiro would more likely parry, dodge or catch the Buster Sword, to which at least Cloud can pull free from.
There is one caveat: Can experience and skill fully prepare you for something you've never seen before? While Cloud's swordplay is something Ken can easily work around and his Limit Breaks being similar to ki based martial arts Ken already has beaten (he also should be able to null Cloud's Blade Beam and Meteorain as those are essentially chi constructs), but literal magic and fantasy monsters would come to Ken as "supernatural nonsense from geeky media that Bat for some reason likes that the nuclear war made sure to get rid off" does seem something Ken would be genuinely caught off guard by given how different it would be from the enemies he has fought in his career.
The point I am trying to get to is that Cloud does have enough skill, reflexes and senses of his own to avoid being taken out with the opening move and can realize what's he's up against and try to take measures for it. There's one thing to take into account: Cloud is a surprisingly intelligent fighter, despite his comparatively lower skill (and certainly he's nowhere near the battle genius Kenshiro is), but he does have a good grasp of combat and how to efficiently approach different situations. In the very first boss fight of FFVII he warns Barret that he should not attack enemies carelessly (the infamous "attack while the tail is up" meme, but it was actually a mistranslation, the original line was more like "
if you attack..."), and in the game's tutorials, which Cloud himself gives to rookie fighters, he explains it's a good idea to evaluate the enemy, look for weaknesses, be aware of "sneaky" moves, don't overestimate yourself and even use the Sense/Assess Materia to get info (which reveals basic parameters, weaknessess, resistances, strengths and even useful tactics).
What I am trying to get at is that, I do think that Cloud would realize how horribly outmatched he is against Ken in a close range fight and will try to play it safe with ranged abilites, such as Magic, Enemy Skills or Summons. Cloud does suffer a bit from RPG non-canon tactics syndrome, in that we don't have a clear example of it (but to be fair his only display of fighting on his own in canon was Advent Children and in that movie he had all his Materia stolen by the bad guys when he went to pick it up to use them againt the villains to begin with), but sorry I digress.
If things can go to distance things are more favorable towards Cloud, by that point of the game he does have a lot of ranged options, many spells track the opponent location to take effect or have rather unconventional shape (for example, Frog Song is a sound that turns people into Toads and puts them to sleep, though Ken resists the latter), quite a few of his haxes do work on Ken (Time, Death, Transmutation, Absolute Zero, Gravity, Dimensional BFR to the Void), and he can also turn them into AoE or multi-targetting thanks to the All Materia. Not to mention, Cloud could also resort to Haste and Slow to create a speed difference with Ken (double his own speed, halve his opponents. Though I don't know if this is applicable with equalized speed).
Now, I am aware that Ken has many powerful long range techniques as well, such as Tenha Kassatsu, Hokuto Gōshō Ha or Tenshō Honretsu, as well as duplicating himself to give chase and bombard Cloud. However, please correct me if I am wrong here, lethal as those moves may be they are more straightforward Ki moves, something Cloud actually could try to dodge (if there is one thing Cloud has practice at is dodging crap shot at him, most of the Midgar section of VII has Cloud and his team being shot by machine guns, lasers, missiles from many enemies at once and every angle anytime they went into a Shinra Facility) and maybe the Reflect spell does work here, while in theory it reflects magic, in practice it bounces back any attack considered non-physical that doesn't explicitly bypasses barriers, energy moves are actually included. Tenha Kassatsu is the one I am ambivalent on, as it's pretty ambiguous depending on the media of what shape it takes or if it's invisible or how much range it has. I know Ken duplicating himself is also possible, but as I mentioned, Cloud does have ways to make his spells and different moves that can target all the Kens present.
Another Materia that
really helps Cloud here is Long Range, which allows his physical attacks to reach several meters from where he is physically located. This essentially helps further to avoid getting close to Ken. Though I don't think it would get a surprise hit on Ken. If Ken saw Cloud faraway swinging at the air, he'd realize something must be coming and prepare to defend anyways.
I know it looks like I am hyping too much Cloud's magic, and to be fair I kind of am, but I thinks it's more fun to try to go through all the possibilities before declaring the winner instead of simply looking for the quickest one-hit kill.
