The expression “bailing them out” can be used to refer to someone who helps someone escape from a difficult situation. That might refer to bailing water from a leaky boat or might refer to posting bail to secure someone’s release from prison while awaiting trial. It certainly doesn’t refer to baling which is the creation of a bundle (such as a bale of hay). I’m sure that a farmer would appreciate some help at baling time, but such help would hardly qualify as rescue from a difficult situation.
The expression “woe is me” is used (usually in a sarcastic manner) to refer to someone who feels that their situation is sorrowful. It is not “whoah is me“, I suspect that the word whoah was invented long after the expression “woe is me” became commonly used.
Made up words such as worserer and worstest. I can understand that people such as Keith Olbermann  may find it a challenge to describe some of the bad people in the world, but he is articulate enough to rise to that challenge while using real words.