A truly mad project. It sounds fun and ingenious, but the issues that would come from it far outweigh the benefits.
First, since it seems that the entire wing of the airliner module is ment to hold passengers, whenever it rolls, everyone in wing tip seats will be thrown all over the place(which is a issue I have identified with spanloader aircraft in general). Second, while moving people between aircraft isn't an issue, how you plan to move their luggage is a totally different matter. And third and most obvious, the whole midair docking is, to put it lightly, enormously dangerous. One slip up, and you have an air disaster above all air disasters. And good luck attempting that in bad weather.
Overall, while I can see the thought process that created this system, the problems with it's overall design, issues with transfer, and extremely hazardous docking concept make this design much too dangerous to ever attempt.