What jumps out at me about the socks thing and friends...
Yes you are right to think he should buy the next pair. But don't threaten to do so, or embarrass him. Just do it. let him go buy more. When he's out, he's out. Too bad.
It's more of "matter of fact" attitude.
Let him fail, fall due to his own lack of foresight or gratitude .
I wouldn't say a word about it.
EXACTLY. Shaming them in front of their friends isn't the goal. With the socks thing, I'd just say "Hmm, you don't have any socks? Didn't I just buy you a pair?" and that would be it. If he then asked for me to buy him another pair, I'd simply say nope, and leave it at that. And ignore the haranguing. When he whines about the fact he doesn't have the money, I'd reply "Hmm, you have a problem. What are you going to do about it?"
Actually, that line "Hmm, you have a problem. What are you going to do about it?" used to make my kids SO mad, because they know when I said it that I was NOT coming to their rescue. Because I never did.
As for your husband, I know what you mean about talking to him and that not working. You can employ all of the 'active listening' and humility and openness and vulnerability in the world, all that does is make you feel like you've been banging your head against a wall.
I actually do have to give older son daily rides or he would not be able to participate in sports, which is his life. He needs the healthy outlet for his intensity. .
No, actually, you don't. You have a choice here. All you need to do is make it clear to your son first, and your husband second, calmly and matter of factly, that you are unable to continue doing what you've been doing under the circumstances you've been doing it. It will stop NOW. If husband will come on board and start backing you up, you can resume ride duties. But until that time, you can't do it, and it is therefore husbands responsibility to arrange something for son to get to his sports games. Whether husband pays for cabs, or arranges another kids parent, or gets him a bus pass, or WHATEVER, husband is the one who has to make sure he gets there, by whatever means it takes.
If you landed in the hospital, who would take him?? Your husband is perfectly capable of figuring this out, is he not?