My experience has been that the best way to migrate to AS3 is in two phases - first structurally, and second syntactically.
First, do rounds of refactoring where you stay in AS2, but get as close to AS3 architecture as you can. Naturally this includes moving all your frame scripts and #include scripts into packages and classes, but you can do more subtle things like changing all your event listeners and dispatchers to follow the AS3 flow (using static class properties for event types, and registering by method rather than by object). You'll also want to get rid of all your "built-in" events (such as onEnterFrame), and you'll want to take a close look at nontrivial mouse interaction (such as dragging) and keyboard interaction (such as detecting whether a key is pressed). This phase can be done incrementally.
The second phase is to convert from AS2 to AS3 - changing "_x" to "x", and all the APIs, and so on. This can't be done incrementally, you have to just do as much as you can in one fell swoop and then start fixing all the compile errors. For this reason, the more you can do in the first phase, the more pain you avoid in the second phase.
This process has worked for me on a reasonably large project, but I should note that the first phase requires a solid understanding of how AS3 is structured. If you're new to AS3, then you'll probably need to try building some of the functionality you'll need to be porting. For example, if your legacy code uses dragging and drop targets, you'll want to try implementing that in AS3 to understand how your code will have to change structurally. If you then refactor your AS2 with that in mind, the final syntax changes should go smoothly.
The biggest pitfalls for me were the parts that involved a lot of attaching, duplicating and moving MovieClips, changing their depths, and so on. All that stuff can't really be rearchitected to look like AS3; you have to just mash it all into the newer way of thinking and then start fixing the bugs.
One final note - I really wouldn't worry about stuff like import and override statements, at least not to the point of automating it. If you miss any, it will be caught by the compiler. But if you miss structural problems, you'll have a lot more pain.