Just a couple points before I tune out of this forum post:
“I would be much happier in a marriage to a girl who would constantly scream at me for not having been born Yeshivish as opposed to being married to a more open-minded girl who would give me a hard time for being too machmir on many inyanim.”
Why would you want either of those? Wouldn’t you prefer to be with someone who takes pride in your background and how it led you to who you have become today? Don’t you want someone who will respect you as opposed to someone who looks down at your background, which reams of arrogance as almost no one has a perfect background.
Also, what does being open-minded have to do with being too machmir? Technically if you are open-minded, that would connote that you would be open to the idea that someone has a more stringent view on halacha than yourself (that opposite also being true, which I think is what you meant).
Don’t you think there are better ways to assert our individuality is by being more machmir than our fellow? If it helps you with your Avodas Hashem, then by all means. But being machmir for the sake of being machmir isn’t a healthy approach for growth. Since this is a deeply personal question for each person, I’ll leave it at that.
“The shadchanim told me that the girls would rather marry closet apikorsim and then simply divorce them, ”
while bochurim like myself or my roommates whom are considered “100% Leshem Shamayim” are טמאים for not being born Yeshivish…”
I think it is inappropriate to look down on a small subset of the religious Jewish community who experience issues with their own system of belief,, and isn’t really particularly relevant to this forum post.
Our job is to focus on the factors we can control, our kavanah in davening, learning a seder, improving our middos, etc. Provided we do our hishtadlus (Unfortunately you will have to do more than someone who grew up Yeshivish because you are a bit different, and you should celebrate your differences, even if it makes dating more challenging for you), Hashem will send us the proper person for us based on who we are. You can be certain that whoever you marry certainly will not consider you Tamei when you meet her.
As a final point, do you know for sure that a BY girl is ultimately the best fit for you? There are many wonderful women who moved more to the right over time as you have. Is it worth marrying a cookie-cutter BY girl when there could be a better match for you outside the system? What creates a Shidduch crisis is when marriage is used as a status symbol i.e. I will only marry someone is who is _________ (Tall, blond hair, blue eyes, LWMO, MO, MY, BT, BY, etc.), which you have alluded from your own personal experience some of the difficult you experience. But that shouldn’t justify our own marriage choice because others might fall into that trap.
Ultimately, this conversation is best suited for yourself and your Rav, who hopefully can give you some guidance as to how to navigate the system. Wishing you only the best and that IYH you should find the right person at the right time for you.