Are you talking about VA understanding the current context of the caret?
Consider:
// spot one in file
using namespace std;
// spot two in file
these two locations are different, due to the using namespace line. Our parser is designed to try and work out your position in the current file, but once you are in a dialog you are no longer in the current file.
You may have noticed that sometimes there is a slight delay as you move through the file before things like the context and definition fields are updated.
Ignoring for the moment the problem of asking the parser "where am I?" you also have timing issues to consider.
Just because this sounds easy does not automatically mean that it is easy.