[adultstudent]

Well as far as the problem of having a positive formal charge on a halogen....
I just checked my undergrad orgo book (Ege) for halogens and electrophilic aromatic substitution, and it claims that since all atoms have an octet when the halogen has a formal positive charge that it is a major resonance contributor. This is contrary to what Klein is saying. I personally find Ege's explanation easier to comprehend.  

No, it doesn't contradict Klein's claims. It's just an additional way of explaining how ortho,para substitution is more stable (and therefore more feasible) than meta substitution. What this method does is analyzing the stability of the intermediate. Let's say you want to make the aromatic electrophilic substitution with group A: you draw the intermediate at the position you intend to place group A and proceed to draw the resonant structures of the intermediate. If you look at the drawing I have provided you will see that, when you place the substituent A at the ortho position, you get four different resonant structures, whereas when you place it at meta you only get three. Moreover, the extra resonant structure you get when you place it at ortho allows all the atoms in the ring to have an octet, which makes it all the more stable. I know, I know, that extra structure has got the positive charge placed on the halogen, but I guess that such unstable situation is somewhat compensated by all the atoms in the ring having the octet.

Please, do not mistake these resonant structures I have provided here (where the delocalized charge is positive) with the other resonant structures we have been discussing all along (where the delocalized charge was negative), the sigma complex. The ones I have provided here are those for the intermediate that forms once the substitution reaction has begun, whereas the others we were discussing are those that exist before that happens. Notice that those were intented to assess the degree of activation/deactivation of the ring at different positions, whereas these I provide here assess the degree of stability of A's intermediate at different positions.

At the end of the day though I doubt there is one fully correct answer. There are many models in chemistry that we use which may have no bearing on reality. However since they are useful, we use them. (Hybridization is a useful mental construct but several have said it is unclear if it has any basis in reality. Phosphorus is claimed to be able to have more than an octet because of low-lying d orbitals while others say it's not a d orbital but rather some other orbital (I forget the specifics). The Zimmerman-Traxler transition state for aldol reactions does an excellent job of predicting the stereochemical outcome of the reaction, but there is not direct proof of the transition state. There are numerous examples where things are more complicated than our mental constructs imply, yet it is useful to employ the mental construct so we do.)

Yes, I agree. More than how realiably a model represents reality, what's really important is that it allows us to put what happens in terms that our left brain can understand and make sense of (even if it's just some kind of self deception). More importantly, the model has to allow us to extrapolate that explanation to other similar situations, so that we can predict what's most likely to happen, that's its usefulness. Bohr's model of electrons orbiting the nucleus of the atom does not represent what really happens at the atomic level, but it is nonetheless very useful when it comes to predicting the amount of energy that is released/absorbed when an electron changes from one energy level to another. If a model works well for predicting what we are interested in, its simplicity is probably more important than whether or not it really represent what's really happening "down there". And let's not forget that at those quantum levels things are probably beyond our human capacity to comprenhend, it's not like they are nanoscopic marbles, more like waves that collapse into particles when an observation is made, imagine if we had to take all that into account when explaining a chemical reaction.

[adultstudent]

Just for clarification, here is one of the drawings that I should have attached in previous explanations.