No, you are making it too complex. He is completely wrong about and does not understand the main cornerstone/premise of Austrian Economics (which, many people including myself simply describe as "economics"), and it very simply stems from the fact that he made a statement that re-allocating economic decisions of others doesn't lead to less efficiency when that statement flies in the face of everything logical you can get out any study of economics. If people want more apples and somebody else decides to re-allocate to oranges by stealing people's shit, that isn't going to lead to more people getting more things that they desire. It really isn't that complex, economists simply get buried too deep in things that don't matter because they want to understand something that can't be completely comprehended.
Do you have an economics degree by any chance?
I'm about to get a degree.
Your argument falls apart once you introduce externalities, public goods, several other game-theoretic examples, etc. You basically argue that the prisoner's dilemma does not exist in real life and that it's impossible to construct a scenario where there is a solution which every individual would prefer to the initial situation but which could not come about by free trade. In neo-classical economics the Coase-theorem argues that without transaction costs this would actually always be the case. However, it's pretty easy to argue that in real life there always
are transaction costs and that the efficiency of free market solutions therefore depends on how low or high they are.
Walter Block and Guido Hülsmann try to adress those issues in their follow-up pieces to Caplan's arguments. You need to go pretty deep into the basics (epistemology, philosophy of science, etc.) in order to get their arguments. What they argue is that there is no way to
know whether one state is prefered over the other, unless people
act accordingly. Caplan argues that this does not need to be true. He could rank every imaginable action/allocation/outcome in his head and know that there are some that are better than the one that he chooses, because the better ones are not reachable without the use of force. Dr. Block dismisses this argument because he argues that there is no basis on which to judge whether or not
other people prefer one state over the other unless they act and he also points out that their preference relations can change as time goes on and that therefore asking them after a forceful redistribution makes no sense. Etc. pp.
They then go on and discuss the difference and importance of analytical / synthetical, a priori / a posteriori statments and probability theory as a foundation for science, etc. The whole debate admittedly goes a little bit over my head (I understand their points but I'm by no means equiped to make a judgement on whose arguments are "correct" or on which side "won" this debate).
Of course I could be misrepresenting their views by shortening it so extremely. Go ahead and read the responds yourself if you're interested.