To be honest falling in love tends to be the big solvent that dissolves the boundaries of risk aversion and lets you do dumb stuff like trust in a future with a woman. At least its been that way with me. These days it just would have to dissolve a wall of red pills. The wall has got thicker over the years. It really would take a big does of falling in love these days.

That is not a helpful answer but tis probably true. What I can say with the lady I am with now and have been with for over 15 years is that one day I acted like a dick in front of her family, through fear of getting ripped off (too complicated to explain). When I came around to how I had been a dick, I apologised and wondered how the situation could be fixed. She told me not to worry, she had already paid the money that was needed "because if you fall short on something, its my job to cover it" she said gently. That's what sold me. She didn't side with her family but helped me when I had been a dick.

Fast forward. I am always covering for her when she falls short these days. If I ever dare say so, I get my head bitten off for reminding her. Funny that, I was grateful back then. Didn't vet enough for pride! But still, there are no perfect people.

You are way too worried about finding relationships dude

From what I've gathered

too outgoing, independent

Your key word there is TOO. Too outgoing and too independent. Why are you wasting your time?
You're going about this completely the wrong way. You are ignoring the laws of natural attraction.
You don't find a wife. Your wife finds you. If she meets your standards, then you can accept her. If she's too anything, she's not the one.

I’m going to be single forever, and I want a family.

You need to accept that it's okay to be single forever. You need to be comfortable with the fact you might not ever get married, and might not ever have children. You should be at the point in which you couldn't give a fuck about women, that you can live without them, and be at 100% peace with yourself.

That phrase right there means there is something going unfulfilled in your life that you think having a partner and a family is going to fill that void. You are 100% wrong. You need to take a deep dive into yourself, perhaps with the help of a therapist, and found out what's missing. Then you need to work on filling that missing gap.

No woman will ever be able to make you happy if you're not happy with yourself, and can look in the mirror each morning and be okay with living with yourself, by yourself. When you can do that, you will attract women naturally, with zero effort, and if you stick with your standards and morals, you will attract the RIGHT woman.