Just a couple of observations from my own experience from being involved in an open air team. I have noticed that few people preach the whole gospel, and the rest are oblivious to the fact. Some will preach the Law, but neglect the Cross. When preaching the Cross, they neglect the Resurrection, preaching Repentance without Regeneration.
It would seem that many are focusing so much on the "technical ability" and "proper content" of preaching, than living in the experience they preach of. The sad result is that they see themselves as mere "Enforcers of the Law", than as "Heralds of the New Covenant". This is an understandable conclusion to reach considering the nature of open air work. It is often thankless and attracts much opposition. In a culture that expects results proportionate to efforts, open air preaching appears to be a waste of time, and the one who is not secure in his relationship with God will seek a reason for preaching that will justify the expenditure of his time.
This thread stood out to me because I recently noticed this angry streak in a friend of mine as he preached. To answer Krispy, anger isn't defined by volume, volabulary, or facial features, but by attitude. There is a preaching that pleads with people and there is a preaching that merely tells people off. I realise that God can do anything He pleases, and nothing can truly limit Him, but I find it hard to see how anything but the "sorrow of the world", which leads to death, rather than "godly sorrow" that leads to repentance. As I watched my friend preach, doing little but offend, something that a heckler said hit a nerve, and I suddenly heard a tone of hurt in his voice. At this point the mouths of his hearers were silenced, and his words were heard.
I am reminded of Reidhead speaking of Whitfield "sobbing like a baby" as he preached in Ten Shekels and a Shirt, and Jesus words "Forgive them Father. They don't not what they're doing." Open air preachers would be wise to remember that God desires that "none shall perish, but all shall come to repentance". I personally see my job as a preacher as parting the veil of eternity a fraction so as to give sinners a peek inside. It is a patient labour of leading people from the "seen realm" to the "unseen realm".
It is a strong temptation for the open air preacher to slip into legalism. This is the result of overemphasis of the Law, apart from a firm comprehension of Grace. Personally I was greatly helped by listening to Paul Washer's sermon "Regeneration and Self-Denial". The sermon was birthed out of being asked to preach on Self-Denial. Washer began by saying that Self-Denial is impossible for the Unregenerate. The open air preacher that forgets this is at great risk heaping burdens upon sinners with Pharisaic ferverence.
A preacher's call is to win the lost, not condemn them. To paraphase E James Wilder, a Christian may desire to be judge, but that is God's job, we are called to be witnesses. The job of accuser is taken also, but no Christian should want to be likened to him.