Okay this is really great. This is exposing holes in my explanations. Thank you for writing this up.
All of what you said is true, with regard to your examples (e.g. change from A-> B with respect to driving). I doubt anyone can deny that. Let me just fix up some of my points before moving onto the bigger issue.
> The problem is people think habits are the only solution
This is a biased statement, mostly from my experiences. I used to think this way, and am projecting a bit. But I have witnessed people really relying on discipline and habits to live their lives. So while it may not be the only solution, generally when people think of change from A -> B, it means doing B an awful lot so that you get used to it.
> You can change yourself via a bottom up approach too.
This is a good distinction. My view is that most bottom up approaches that are used are actually top down approaches. The true bottom up approach that I take is watching Netflix, playing videogames, sleeping until noon, whatever. I know there is little justification for my claim here, but at least that is what I believe and it's interesting. Maybe it will clarify as to why I think that is the solution.
In a way, if you need to force yourself to meditate, I suggest you don't (my meditation teacher will be very angry that I said this, but I believe it).
The only way that I was able to deal with major psychological blocks and difficult problems was in actually doing A forever (or at least intending to do A forever) in the A-> B example you gave. The mind, as it turns out, is a complex system of beliefs, with beliefs on top of beliefs, next to beliefs, and all that.
I had only couple sessions of CBT, but it seems they don't go all the way down. Or if they get stuck at some belief, there is no real way downwards. The same is true with Tony Robbins methodology. They talk about limiting beliefs, but they are not entirely sure as to why limiting beliefs do not go away (or why you have to "combat" them for a majority of your life).
The only way to dissolve limiting beliefs is to actually believe it further, create excuses for it, create fiction for it. For instance, if you believe in conspiracy theory to justify your anxiety (and you don't want to believe it), and are in this sort of weird dual-state, then I actually encourage belief in conspiracy theory.
If you find yourself lying to yourself all the time, or deceiving yourself for variety of reasons (this hiding/distorting property of mind is actually a feature, not a bug), then I say keep lying to yourself, help yourself lie to yourself, etc.
For a simple (albeit flawed) justification, just notice actively, consciously espousing the "bad" solution is actually the only thing you haven't tried in that particular problem context to a great extent. Very few would do this. Thus your mind is sort of limited in doing this, and in doing this sort of "bad" thing, you can solve some pretty untractable problems.
Maybe I am spewing BS from your perspective, but these are strategies that I have used for some time with good success, and will continue to use. It only makes sense that I represent the strategies I use.
Also another thing is most of the time you actually don't know why you are doing something (or why you aren't doing something). People blanket it with "laziness" or evolutionary whatever, but from my experience, once you understand your reason for a habit, you can actually choose or choose away from it. And understanding, say, why you play videogames every day might involve actual, belief-level changes in metaphysics or social norms or how physics works. Who knows. All these beliefs are ultra connected.
But given this, habits impose a kind of short cut towards solving your problems, in a nominal way. And you can get real addicted. You can build a castle of habits, more disciplines, more Triggers (to use Fogg methodology), etc. But if you actually change you don't need triggers. You trigger yourself. You think about math problems in your sleep.
And this castle of habits is very fragile. You look disciplined. You face a lot of pain. But you are no fun. So for people who have crazy regiments and whatever, I don't really try to talk about this stuff. If you need it, you need it. It's not necessary that everybody sort of does bottom-up.
But if the block towards bottom-up is not mental but rather lack of knowledge/experience, then I think it's worth not using habits whatsoever. Wake up as late as you want, despite what the consequences might be. And maybe if you are not in a situation that makes that feasible, then you might need to make room for psychology. But a lot of people impose these constraints even when they don't need to (e.g. weekends, trying to read books and stuff in their free time, etc.). It's really hurting psychological progress.
I am not sure if I really answered your comments, but feel free to poke any gaping holes in what I said.
EDIT: Okay, reading your post again and adding comments. The A->B is a simple model for describing different opinions about how one views psychological change.
The vast majority of people, when they agree that B > A, would say you need to keep doing B. You keep doing B, then you get used to B, and your resistance to B is fear, or something evolutionary, or laziness (I think this covers about 95% of people's explanations). So you are suggested to keep doing B. Now let's say you didn't become numb to B but that now, like in driving, are just completely used to it. This happens a lot and is how a lot of things do work.
But for some really, critical, self-defining problems, doing B is not the way to go. Good example might be "thinking positive thoughts in a negative state". So here A would be "think negative thoughts" and B would be "think positive thoughts". Everybody sane would suggest that if you are A, and you want A->B, then you should keep doing B. As in, in a negative mood, you should put effort into thinking positive thoughts.
But at least with me, this doesn't really work. By and large forcing positive thoughts into negative states is hard (part of it is how it is defined) and over time you don't get "used to" positive thoughts. (and if you don't see negative thoughts anymore using stay in B method, most likely you no longer have access to that negative thought but it still exists under the hood, rumbling and affecting everything else. it's just unobserved)
This is different from driving example because there B is not fully mapped out or known. You are driving and you are unskilled, so you are mapping out B until you get used to it.
In this positive thoughts in negative states example, you basically know what B is like. Maybe you haven't accounted for every possible state, but similar problems keep coming up.
Thus I would say in this situation you need to keep doing A. So I am saying in a negative mood you should keep thinking/actively encouraging negative thoughts. Which, I would imagine, is surprising (and perhaps crappy) advice.
But this actually worked for me! This is what got me to change my thought patterns.
A thing that might jive your thoughts: It is well-recognized that thinking positive thoughts in negative mood is hard. Try doing that, it's really hard. But try the opposite. Try thinking negative thoughts in positive mood. For me, it's equally hard to think negative thoughts in positive mood as thinking positive thoughts in negative mood.
The mind doesn't care. You just gotta align with it. And if you align with it, you will understand it (given enough time), and be like "Oh, this is why?" And then you move on, the issue doesn't scream anymore, and you can live.