Money has it's limits, growth and experience does not.
What a mess, Bubs :( :mad: :coldfeet:
You sound like you've got good overview of the mangled interactions/relation between your family members.
From the list, it seems your parents didn't provide much in the way for him to know how to be self-sustaining. Kudos for being a good big sis and helping him with those things. Keep playing the role of the good big sis. Teach him to be self-sufficient and self-reliant when it's appropriate (as you've been doing), according to his needs and your convenience. But don't do it to the point that you're enabling him. Who knows? He may have to sleep on a beach or a sidewalk somewhere before the "click" happens.
As you said, "Money has its limits; growth and experience does not."
It sounds like you and your brother have a close relationship. So naturally, you care for him and thus prefer not to endure having to seeing him suffer. You've got a close relationship with your baby, eh? And, I'd guess you to have some trepidation about just how the birth of your baby is going to go. But beyond what you know to be a possibly painful birthing process you believe and trust that you're both going to get through it. And you will! Your brother is going through his own birth of becoming a man. Let him. Get in touch with that place in yourself where you know you can trust yourself, where your strength and confidence lies and transfer some of it to him. Believe and trust with all your heart that he can become his own person through the natural process that he's going through. As Abstract mentioned, help build his self-esteem.
I don't know how accurate your view of your father's maliciousness is, but it doesn't matter whether it's accurate or not. You and your hubby just have to agree on how the two of you (united) will handle things with him and work on deflating the triangulation.
It's likely your father will try to go through your hubby and/or another family member again and do something similar. Simple courtesy, directness and honesty are need: "Thanks for your offer. I'll talk to R about it. We don't keep secrets. I'll let you know by tonight if we're interested. Or a simple "Thanks for thinking of us, but it's not something we're interested."
As for the triangulation between your father, brother and you, IMO you've given your brother enough of your view, your insight, as to how your father is. Start taking the high road now and be the mature one, i.e. "I'm sorry he (your father) got you involved in this. What you described isn't my and hubby's view of the situation. As far as we're concerned, it's not a big deal. I suggest that you not let it be a big deal either. I love you. Is there anything else you want to talk about?" Remove the focus of how f_k'd up your father is, the causes of the difficulties your brother is having, your own problems/issues between you and your father, and just deal with being there for your brother when/if he needs you.
Be interested in your life; be genuinely interested in your brother and his life; the rest of the stuff is just b.s.
You're great sister, and you're going to make one heck of a good mom!
Drew :hug: