As a self-professed ignoramus on the topic, I think there are several biases that would naturally make people feel that there is a terrible crises and constantly getting worse, even if reality doesn't necessarily match that view.
1. Focusing on absolute numbers, not percentages. If 5% of 18 year olds in 1990 had a difficult time getting married for various reasons, that may add up to 50 people. If the community grew 3-4x since then, and unmarried rate remains at 5%, you'd expect to see 150-200 girls added to the list each year. That's a large number that keeps growing, harder to look away. Just like you feel the world is full of tzaddikim when you attend the Siyum Hashas, and the world is full of low lives when you're at a football game. Nothing changed except your familiarity and perception.
2. Some of those 5% don't get married long term, and every year the list of unmarried singles grows on top of the previous year.
3. Network effect: With social media and technology, the world is smaller than ever. Shadchanim have access to infinitely larger networks than 20-30 years ago. Deluged by older singles that were previously out of their network, it's inevitable that they will perceive an exaggerated version of reality.
Does this mean that the crisis doesn't exist? No, and I'm a dumb know-nothing. But I think anecdotal evidence from shadchanim does not necessarily paint an accurate portrait. There is a need for real data and less anecdotes.
Hard to properly solve a problem when you can't prove it even exists.
