Tax planning can involve unbelievably complex maneuvers. Some of the strategies may be less certain than others. As a strictly opinion-type question or series of questions, consider the following.
In completing any tax planning for a corporation for which you are the CFO, to what degree would you be willing to be aggressive?
For instance, would you only want to take a reporting position that is almost certain to be upheld? Or would you be willing to really "push the envelope" and take positions that are arguably defensible but subject to very likely challenge if the Internal Revenue Service audits the return?