And that's probably why things are where they are now.
I think the shidduch system works for 90% of people, so those numbers aren't bad. But there does need to be a solution for the 10%.
Finding that solution is totally the $64,000 question!
You makes some very good points, but it’s hard to see a practical way of implementing the above in a non MO setting. How do you draw the line with only the 25+ crowd (25 for a boy is probably too soon) chatting by the kiddush etc. and expect younger people to desist? How do you prevent the chatting from descending to what a right wing town would consider “kalus Rosh”?
Having dedicated 25+ singles events is probably not going to work since these are notorious for being poorly attended by quality boys.
So good ideas in theory but extremely tough to implement in practice ....
You're describing it as a bug when it's actually a feature. That feature comes with some collateral damage. I don't know what the right answer is to avoid that damage, and I feel terrible that it exists for those like yourself that are affected. But it's not so easy to tell the 90% (or whatever the percentage is) that it works well for that they should take a new approach to dating/marriage that's worse (certainly in their minds) for them but reduces the collateral damage.
I definitely understand this tension and want to keep the normal system. How about rebbeim speaking privately with people that everyone knows aren't gonna be "on the top of the shidduch lists" and privately encouraging them early on (especially girls, where time is of the essence) to not feel embarrased to be pro-active about trying to meet people. If they are still living at home or seminary or yeshiva, how about telling friends, trusted teachers, rebbeim, etc. to please always be thinking of them and not just for blind dates, but for a joint shabbos meal. Like, if the girl is very overweight or has a disability, why not let the guy meet her on Shabbos and the wife can privately ask afterward if he'd like to go out with her without breaking her heart with a painful blind date and rejection? Maybe after having a few laughs or a comfortable time that guy is willing to try a date? More informal set-ups can be great, are still "shidduchim" but not from resumes and these Shabbos meals aren't going to "ruin" the shidduch system for the average kids.
As a slightly related example, I have a close FFB Sephardic friend who affiliates with Chabad and they are quite well off. Her handsome and erliche son came up in an OOT school (the local frum school, no Chabad school in the city), feels more comfortable around the ashkenazi kids he grew up with, has decided he wants to go the Yeshivish route, is now a top learner in Lakewood and told his parents he'd really like to marry a Yeshivish girl. The Lakewood shadchanim are definitely only sending him "non-standard" shidduchim, to say the least, and they would be licking this family and boy's boots if his parents were slightly different. One told her "why would a normal ashkenazi girl marry your son?" I straight out told her not to count on them and that she is going to have to pursue local people that she knows and know their beautiful family to try to find him a shidduch that way. It would be a shame to wait around for the system to fit them in. As a boy, he will eventually find a great shidduch, probably from someone who knows them (although I've seen lovely hareidi Sephardic girls have this kind of problem and kind of "miss their window").
I think my BT hevre intiutively knew that we were going to have be pro-active (because we had no frum parents to help us). One of the reasons I didn't stay in EY after seminary was because I knew I wasn't really going to get set-up there because I didn't fit in (learned at a Yeshivish place, love Chabad but don't want to be Lubavitch, didn't really want to date MO but felt comfortable in that environment, my parents are divorced, etc., etc.). Men found me attractive and I never lacked for male attention and dates so that wasn't an issue for me (and half the battle for a girl), it was more figuring out my place in the frum world and how to meet appropriate people in appropriate settings. I'm SO glad that I decided to return to the US and live in the more "modern" neighborhood of my large city (not Denver) where me and my friends could have and create some of these opportunities. It's actually a miracle that we took the initiative to do this on our own but our haredi kiruv rebbeim (both Lubavitch and Yeshivish) never discouraged us because they also know this and just quietly hold BT's to another standard (which is actually good in this case). Maybe we don't change the whole ideal shiduch system for FFBs but then we and community leaders try to be aware and active about privately encouraging these singles to seek out (or create) mixed opportunities to meet people.
For example, the rav for the girl in this article might have wanted to say, "Listen, I don't normally advise this but you should be not only actively seeking out formal shidduchim but advocating for yourself to others to actually PUT you in social settings where guys can get to know you as more than your disability on paper and it could lead to appropriate dating." She might not have wasted those precious years waiting around for horrific shidduch dates with Pedophiles and maybe when she was less bitter and angry, could have been meeting and making a better impression on a wider pool of guys in a mixed setting. Ok, that was an extreme example but y'all get my drift. Maybe hareidi Rabbis and Rebbetzins and community members as a whole can have some introspection and the courage to have some of these private conversations, maybe that might help? Maybe I'm also in LaLa land, spent too long now OOT and this will never happen!