Distributing C Corporation has some assets that would produce a substantial gain if sold, and other assets that would produce a substantial loss if...

Distributing C Corporation has some assets that would produce a substantial gain if sold, and other assets that would produce a substantial loss if sold. Its goal is to transfer assets to its shareholders, but in a manner that would enable it to defer the gains, or at least deduct those losses against the gains.

If Distributing C Corporation asked your advice, what issues would you raise?