I think the key to knowing the 'real' Cloud is to look at the events where you aren't given any choices with him. He cross dresses, is thoroughly called out on sexism, he rides a dolphin, he's made to join a parade, fight an arena tournament single handedly for a rich man's amusement, ride a chocobo for freedom, the list does go on a bit. Invariably he's kind of this put-upon character who wants to act cool, but he gives into people's demands easily.
This goes right up to even Advent Children, where despite managing to seem like he's absolutely abandoned his friends, all it takes is being shamed by Marlene to really set him right. An 8 year old girl chastises him and it WORKS, which is some understated comedy gold lost in all of Advent Children's melodrama. In some ways Cloud never stopped being 16.
I guess my point is that humans don't have a single "true nature".
Ultimately, your points here fall into the "how I percieve you" category of characterization, which is informed by your personal background.
Cloud could be a character consisting of act A, B, C, and personality trait X, Y and Z, but ultimately who Cloud is, or who anyone else is, is a matter of which of these acts and traits you narrow down on based on your particular biases. Furthermore, this act of characterization is colored by your particular values as it pertains to whether you think any of those particular acts or traits are good/bad.
For instance, I never saw Cloud as being someone who easily gives into people's demands. I think personally, there are more examples of Cloud being assertive throughout the game - although, like any human being, you also see him being uncertain and be swayed by other people.
Also, as I said, I think the most important thing here is realizing that Cloud is an amalgamation - as are all human beings.
Fake Cloud is also Cloud. One cannot sepparate Soldier persona Cloud from player Cloud, from post memory-fix Cloud. They are all facets of Cloud and Cloud's personal history, and those facets as a whole is what makes up "the character Cloud".
Tying this point back to my point on character amalgamation and perspectives being changed by biases -
Even if I were to grant that Cloud is dorky because he rode a dolphin, you could spin around on a coin there and point to Cloud driving a motorcycle through the Shinra building and out on the high-way, while swinging his huge sword to fight off enemy combatants - also on motorcycles - totally cool, stone-cold killer Cloud.
I'm not arguing he is the latter - I'm simply arguing that Cloud embodies all those facets, and that what kind of character anyone thinks Cloud is, is going to be informed by which of those scenes or facets they make the focal point for their reading of the character, following from their particular personal biases.
Addressing your particular characterization here though :
I don't think it makes much sense to think of the circumstances forced upon Cloud as a basis for determining that Cloud is a person who "gives into people's demands easily."
All non-linear stories force characters down a path. It's not a failure of the character's personality that they cannot move outside of that - that's simply a result of the contrivances of the story as imposed on the character by the author(s).
You can't not have that happen and still have a linear story, and you can't have a linear story and not have that happen to some extent.
The context of what is going on in those events is key to understanding what the character is thinking and their motivation for going along with their circumstances.
Cloud rides a dolphin because it's the most apparent means of entering Junon - he's not doing it because he just loves riding dolphins, or because somebody is telling/forcing him to do so.
Cloud isn't simply made to join a parade either, he goes along with it, again, because it serves his need for infiltrating the facility and going unnoticed.
He doesn't fight an arena tournament single handedly
for a rich man's amusement, he fights in it for the key-stone.
Riding a chocobo for freedom is another example of Cloud being proactive and doing something necessary. He isn't just doing that because he's to weak-willed to resist it.
I think there's a huge distinction between simply doing something for someone else as a result of pressure alone, and doing something for someone else on the basis that it's convenient and beneficial to yourself.
But again, that's a distinction I see because of who I am, and how I think.
We're looking at the same data and seeing two completely different things.
You see that as Cloud as a person who gives into people's demands easily. I see a proactive guy who does what he has to do to make shit happen under circumstances that offer few, if any, choices.
Also, just out of curiousity :
when does this ever happen in the game :
"- is thoroughly called out on sexism".
I can't think of a single scene where Cloud is called out for sexism. I can't think of a single scene where Cloud is doing anything that would call for him being thoroughly called out for sexism.