Here's an idea, let's make it a more natural experience. Let's refuse to answer "stupid" and irrelevant questions. Let's try to get to know the person we are trying to set up and also the person we are trying to set that person up with. Let's stop worrying so much about what is fair or not to the parents and worry more what is fair or not to the kids. Let's not set them up for failure by allowing them these grandiose ideas and expectations and lets teach them to be more realistic especially where support and paying bills are concerned.
When speaking to parents be more direct and ask "what is your son/daughter looking for" and not what they are looking for. Ask more pertinent questions such as how "HE" plans on supporting his family or if he is going to be a long term learner how his parents are planning to support his choices. Stop kowtowing to the old school "the boys parents want support....." that only breeds more problems, promises that are broken, and bills that haven't a chance to get paid.
If support is offered and agreed upon by both sets of parents make a written agreement and include a time frame. you will be marrying off more children after this one.
If the young lady says she wants only a learning boy, then ask her the same question "how do you and your parents plan to support your choices? What happens when you start having children, what then? Are you prepared to have others raise your children? How much does daycare and babysitters cost? Do you know how much tuition costs? Do you think that you can bring in enough salary to cover all of that?
Then make realistic shiduchim. Stop trying to redt a learning boy on a girl who wants a boy to make a parnassah. I have heard that a million times "but he is such a great guy, such a catch, when she meets him she will change her mind". Why should she change her mind? On the other hand if a young man wants to work and wants his children raised at home by his wife don't redt him a young woman who is in medical school. She is most likely very serious about her career and won't give it up to please him, and don't ask either one to change their minds. Don't put them in that position in the first place that they might like each other and then have to be frustrated that they are demanding that one give in.
In addition just because a young man is in yeshiva does not always make him a "learning boy". Many really should pursue a parnasah and not burden their wive's with it. If you are not living and breathing learning, if you do not think Torah all the time, then maybe you can learn part time and work part time or work and then have a shiur in the evenings.
Learn to listen to understand when speaking to young people so you actually hear what they are saying and what they are looking for. If a young girls sounds immature and sounds like she doesn't know what she wants, she probably doesn't so don't waste the young men's time with her. Same goes for the boys. And stop setting kids up on practice dates. No one appreciates being used and then turned down for a second date because it was the boy or girl's first date and they are not going to settle on the person they go out with. Be prepared to like the first person you go out with.
And parents, you know best, if you know your kids are not ready, not mature enough, too interested in having fun or experiencing life before settling down, then don't let other people talk you into setting them up because you are wasting the other young person's time and draining their energy for dating. The dating process can be a very hard and hurtful experience for many. Not everyone can take rejection gracefully.