I have listen to a lot of sermons and started wondering about the following:
1. Is there anywhere in scripture where the preacher/teacher/prophet was trying to get his audience to laugh?
One of the patriarchs is Isaac, whose name means "laughter". God waited until Abram and Sara were 100, or nearly, before telling them he would give them a child; and Sara laughed. Yes, it may have been a mocking laugh, or one of disbelief, but I would guess they laughed in another way when their son was born, and they named him "laughter".
When Elijah was on Mount Carmel he told the prophets of baal to shout louder because maybe their god "was relieving himself". Again, it might have been mocking them, but I'm guessing it made the Israelites laugh.
I'm sure there are many Scriptures in which, if we knew the original languages, we would see a play on words, or puns.
Also, in the OT, Zechariah 3:17 says that God will take great delight in us and rejoice over us with singing. It's not so hard to believe that he might smile, or laugh, too. Just as a parent may laugh and take great delight in the actions of their small child.
2. Did Jesus ever try to get His audience to laugh?
3. Jesus did tell some “almost” humorous stories, like the log in your own eye, with some very deep spiritual meanings, but would it make people laugh?
"log in your own eye" and also "camel going through the eye of a needle" don't sound that funny in English - and also maybe their impact is lessened because we've heard them so often. But it's possible it's different in the Greek, and to people who hear it for the first time.
4. Is trying to make your audience laugh, also making lite of the subject?
No. I used to listen to the comedian "Dave Allen". When he started on stories about religion, God or the church, I told my mother that he shouldn't be making fun of serious subjects - but it was still difficult not to laugh.
There is truth in humour, and sometimes people remember that truth because it has been delivered in a humorous way.
5. Should the teacher/preacher emphasize the seriousness of the subject, by not showing any humor?
No.
It's obviously wrong to say, for example, "doctrine of hell? Ha ha ha, what a silly thing to be in Scripture; no one is going to fall for that one". But telling a humorous story which makes the point that there are consequences for those who don't believe, is not wrong at all.
6. Would humor hurt someone in the audience caught up in the seriousness of the subject?
It might do, but we don't know what people in the congregation are going through at that time or how they are going to react to anything.
I mean, a baptism might be hard for someone who doesn't have children, (that's been true for me sometimes); that doesn't mean we shouldn't have baptisms. A preacher might use the illustration of marriage to talk about the relationship between Christ and the church, and someone could feel hurt either because they are single or because they are in a bad marriage; that doesn't mean the preacher was wrong to use that illustration. The Bible reading might be the garden of Gethsemane and someone feels hurt because they are going through hardship, loneliness and that other people don't seem to understand.
This is why, I think, it is important to offer prayer ministry, or individual prayer or the offer of a chat, after the service, with anyone who may need it. Or if a church has prayer ministry teams, and the preacher knows the sermon might upset/hurt people, give them the heads up beforehand so they can be aware of it.
7. Why do preachers today use humor?
Because we're human beings and most of us have a sense of humour or can relate to humour.
Because people often remember a joke/funny sketch or story/something which goes wrong better than they remember the sermon, long teaching or serious stuff.
Because, as someone has said, we are made in the image of God; he has a sense of humour and he has given us the ability to smile and laugh.
Because humour helps people to relax - and they may have come to church feeling very worried. Or they may be non Christians who will start to listen because the preacher has told a funny story and/or incident against themselves.
Because it's a way of getting people's attention, which isn't wrong; consider the burning bush, Elijah on mount Carmel, Jesus telling Peter to catch a fish which "just happened" to have a coin in so they could pay their tax.
Because it's fun.