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In this n-category café post Mike explained that it's not possible to whisker 2-transformations with lax functors:
Given 2-categories, 2-functors and a 2-transformation as in the following diagram 
whiskering_setup.png
we can construct the prewhiskering  by just restricting  along : 
prewhiskering_incorrect.png
For the postwhiskering  we encounter a problem though. The diagram 
postwhiskering_incorrect.png
does not compose to a component 2-morphism  filling the square since the compositors point inwards. Using oplax functors/transformations clearly does not solve the problem either.
This is strange, since in the 1-dimensional case we can view natural transformations as functors, and whiskering just as composition of functors:
Given the same setup as above, just with 1-categories, 1-functors and a 1-transformation, we can view  equivalently as a functor , where  is the walking arrow . The source and target functors of  are then given by  and the components of the transformation are given by . Functoriality of  then comes down to functoriality of  and  as well as naturality of . The whiskerings are then given by  and .
Observation: the functor not only supplies the components . For each morphism , the diagonal of the corresponding naturality square is part of the data as .
We can already see how this categorifies: in a suitable definition of lax 2-transformation, we're going to have the diagonal as part of the data along with 2-morphisms filling the triangles. To be fully explicit, we have the components 
components_correct.png
The prewhiskering is given by restriction as usual, and the postwhiskering now works because in the diagram 
postwhiskering_correct.png
the 2-morphisms pointing inwards towards the diagonal compose.
Of course there are coherence axioms to take care of, but this doesn't lead to problems since lax functors compose, just as in the 1-dimensional case.
Concerning this I have two questions:
How do you propose to, for example, compose these “natural transformations” vertically?
That is, if  and  are natural transformations in your sense, how would you define ?
Good point! Extending the definition, we could have arbitrary zigzags of 2-morphisms filling the naturality square. I don't see how this fits the transformations-as-functors pov though.