Thanks for the interesting and fruitful comments. There are properties that it makes sense to say are emergent. Consider the property of being a heap. A grain of sand is not a heap. But add 9,999 grains to it and one definitely has a heap. Somewhere between one grain and 10,000 grains the heap emerges, though one will be hard pressed to say exactly where, and why adding one more grain should suddenly make a difference. Perhaps you are saying that intentionality is like this. At a certain threshhold of complexity intentionality emerges.
But note that emergentism is a kind of dualism: what emerges (intentionality) is radically different from its emergence base, mindless matter. Since emergentism is a form of dualism, albeit not a form of substance dualism, it cannot be used to make sense of Dennett's position which eschews as unscientific every sort of dualism, not just substance dualism.
Note also that it cannot be Dennett's view that original (intrinsic) intentionality emerges. For he explicitly denies that there is an original intentionality. (For example, at the end of "Fast Thinking in The Intentonal Stance, p. 337: "There is no such thing as intrinsic intentionality . . . .")
This implies that all intentionality is derivative. The intentionality of smarter systems derives from that of dumber and dumber subsystems until we arrive at subsystems so dumb that they are utterly free of intentionality (like the solitary grain of sand that is 'heapless').
Intentionality is a useful model for understanding the design and behavior of a system, but I think we must be careful not to grant it some sort of mysterious soul-like status. Obviously a stone has no intentionality, while we have it in spades. But I think Dennett has done a good job of showing how intentionality could ramp into existence gradually, once matter has organized itself into primitive replicators. If a simple organism has over eons evolved cellular mechanisms for engulfing food, then we can read intentionality into those new mechanisms and structures (they are "for" eating), though nothing inexplicable or mysterious has happened.
You say that intentionality is a model, and then you say it can "ramp into existence." There is a tension here. If something comes into existence then it is real and not a mere model of the real. Are you perhaps conflating the intentional stance with intentionality?
Suppose we "read intentionality" into some cellular mechanism. No doubt we can do this just as I can ascribe beliefs and desires to my chess playing computer. But it doesn't follow that there is any intentionality in the cellular mechanism or in the computer. Note also that ascribing is itself a case of intentionality. So if there is no intrinsic intentionality, then my ascribing is intentional in virtue of some other entity's ascribing intentionality to me -- which appears to ignite a vicious infinite regress.
In Dennett's view even the mental mechanisms that underlie our consciousness (with all its rich and multifaceted intentionality) are just a logical extension of that process, a synergistic result of the joint efforts of simpler mental modules, which in turn are the result of the actions of bundles of neurons, and so forth. Our fabulously rich high-level intentionality emerges from all of this in the same way that "performance" or "handling" emerges from the parts of a Porsche. Yes, the individual car parts were designed by the intentionality of German engineers — but our mental parts were also designed by natural selection over deep time.
There is no doubt that you understand what Dennett WANTS to say, but the question remains as to whether or not what he wants to say can be coherently said.
Dennett's theory is ascriptivist: nothing has intentionality intrinsically; intentionality is ascribed or imputed or projected into a system from without. But this ascribing is itself an instance of intentionality, and you want to say that this ascribing is the "synergistic result of simpler mental modules" which are in turn the result of even simpler modules which are "designed by natural selection."
There is a deep unclarity here. How can D's theory be both ascriptivist and emergentist? You said a while back that we ascribe intentionality to primitive cellular mechanisms. Fine. But that implies that those organisms have no intrinsic intentionality. How then can enough of them working together -- syn-ergy -- give rise to the intentionality that ascribes intentionality to them?
There is a vicious circle here. X ascribes intentionality to a, b, and c. Apart from this ascription they would exhibit no intentionality. But X's ascribing is an instance of intentionality that results from the synergy of a, b, and c -- which presupposes that there is some primitive intentionality in a, b, and c that is not the result of X's ascription.
There is also the unclarity of "designed by natural selection." Strictly speaking, natural selection doesn't design anything. Designing is an instance of intentionality, and intentionality emerges only way down the evolutionary road. What Dennett does is help himself to, or presuppose, the very thing he is trying to account for, namely, intentionality.
As for a bridge from causes to reasons, why NOT say that the computer's move is forced by reasons? Yes, we can take an extreme-reductionist view and try to determine the computer's move from the state of its constituent particles, just as we might for a human player, but why bother? We know very well that the computer will avoid mate in one because if it doesn't it will lose , just the same as a good human player. Take any decent chess computer (and there are lots and lots of them - I have about seven or eight myself), and set up an avoidable mate-in-one, and the machine will always avoid it, regardless of the particulars of the hardware or software . I think this is amply sufficient to move from "can be viewed as" to "is". Yes, a human playing a child might lose on purpose (I often did as I was teaching my son the game), but that of course is because a human is a vastly more complex intentional system.
You can impute reasons to a computer or a thermostat or a circuit breaker: it has a reason to trip: it doesn't want the house to burn down and it with it. You could say it senses a surge in amperage caused by a short circuit. But of course it senses nothing: it is just a crude mechanical device. So I fail to see how viewing it as having reasons suffices to show that it has reasons for its 'actions' which of course are not actions strictly speaking.
I think your argument that there is something important left to be explained depends entirely on reifying intentionality, quite unnecessarily, into something more exotic than it needs to be.
I plead innocent. To reify is to make into something real that which is unreal. But intrinsic intentionality is real, and is indeed presupposed as real by any affirmation of derived intentionality. What you and Dennett are doing is denying a plain fact because it fails to fit into your preconceived naturalistic schema. And the cost of that denial is all sorts of absurdities: vicious infinite regresses, vicious circles, equivocations, etc.