Linda, what a beautiful list of parenting goals! I love it, it made me a bit misty. :)
I have lots of family members with mental illness and sometimes I forget what "normal" looks like. Of course it's more than likely that the OPs son just needs more time to mature due to his rough start in life. I still think counseling/parenting classes would be a fab idea.
Thank you. 
I think parenting classes are a good idea to. And I'm always a fan of counseling. Counseling has helped me a lot with tough spots in parenting. Parenting books can help too. My all time favorite parenting book is:
http://www.amazon.com/Liberated-Parents-Children-Happier-Family/dp/0380711346
It's by the same people who wrote how to talk so child will listen, siblings without rivalry, etc. It's lesser known than their other books, but I find it meatier.
He complains that I treat him more like a mother than a friend
You're not supposed to be his friend. I'm sure you are fun and interested in what he's doing, but you are his mother not his friend. He hopefully has many, many friends - but only one mother. And I promise you he needs both! All friends and no mother is no gift to him.
How about not buying pop? He's clearly shown that he can't handle regulating it right now. It's OK to simply not have it.
Yep, even free with coupons isn't worth it. I like the idea of giving it away - or even throwing it away.
I said, oh that's great, so you don't like me then?
He flew off the handle, cussing and swearing about how he can't deal with me, I cause all sorts of problems, etc.
I need to know that he would never hurt me.
I have an almost 16 year old (and two more turning 12 and 9 soon). Let me tell you, they don't like us LOTS of the time (actually not lots but it sometimes feels that way) and absolutely will hurt our feelings many times in the course of parenting. We are trying to raise them to be respectful, resilient, independent adults - it is a lot of work! Given the choice, they'd usually rather listen to music and go out to eat with their friends. Homework, chores, things they've agreed or asked to commit to (like pre-paid lessons or a team sport), family time, visiting elderly relatives, volunteering - we teach/coach/remind/hold them to their responsibilities when they need a little help doing so. It can cause friction! But if we don't, if we are their friend instead of their parent, then we are not doing our job as the parent. It is an often times thankless job. We are not appreciated and are often nagged and disliked. It is part of the job description.
And the cussing - in my family - would be something I'd call him out on. You can tell me your opinions/feelings without cussing. You can be mad; sometimes I'm mad too. But tell me respectfully. (Respectfully is a bit of a relative term... but I draw the line at cursing.)
And FWIW, this is how the conversation would have gone in our house:
Child: "I'm not sharing with you, you were mean and you wouldn't help me."
Me: "That's a rude thing to say. It sounds like you're mad. If you're mad, tell me you're mad."
Child: "Dad and Rob will wear it."
Me: "That will be nice if you have enough money to buy it for them."
Child: "Dad might give it to me."
Me: "That's between you and Dad."
STOP. Don't ask him if he doesn't like you. Don't engage in the argument with him. This isn't about whether he likes you. It's about him being mad because you won't give him money. Yeah, it's rude and somewhat childish. But I suspect his emotional development probably isn't where it should be. THAT is what needs the heavy work. Is he in counseling? Are you? Parenting an adopted teen is tricky. I'd need some expert advice.
Brilliant! I agree 100%!
Okay, so guide me here. I AM a new mom - we adopted him just recently and have had him for 1.5 years.
Ah, so that explains a lot. Here's what I'm noticing just based on your description of the exchanges you've had--your son is a highly proficient manipulator. I know nothing about his background or circumstances, but I'm going to assume that his life up to now has been relatively unstable in some way, and he has had to develop a sophisticated set of strategies to get his needs met, and to control as much of his environment and circumstances as feasible. You see this a lot when you are working with adolescents in foster care or kids who have really unstable home environments).
I said no.
He asked why. (Questions your authority, normal for a teenager, although in this case its more a strategy to continue the conversation than a genuine question because he deep down he already knows the answer)
I said because I didn't want to spend my money on that. (Reasonable response to a question)
He said I didn't need to be rude about it. (Since he doesn't get what he wants, he's using emotional blackmail--you're the one who's being rude, not me)
I asked how I was being rude. (Big mistake, never give them a chance to continue this line of conversation, the only thing it does is give them permission to undermine your authority by calling your decisions into question. Better to say something that will "end" this line of discussion.)
He said I had a tone. (so now he's an expert on paralinguistinc phenomenon? how fascinating)
I said I didn't feel I did, how should I have said it? (Never invite a teenager to correct your behavior!!! Bad idea! It gives them license to say or do anything because you've just basically given them all the power to direct the course of the conversation)
He said nevermind.
Nevermind, I'm not sharing with you, you were mean, you wouldn't help me. (I hear this a hundred times a week from students who don't want to do something they were asked to do. Yes, as a parent, you will do things that are mean, and by not "helping him" what he means is that you wouldn't let him do something he wanted to do. This is not bad, this is you doing your job)
I said, neither of them are helping you pay for it. (Here he has tried to invoke other parties--the classic so-and-so is doing it, so why can't it?)
He said dad might. (Here he is suggesting that he can go around you and get Rob to do what he wants)
I said, Rob isn't.
He said he likes Rob. (His thinking is revealed here: If you give in and do what I want, I'll like you, and I know you are very concerned about whether or not I like you)
I said, oh that's great, so you don't like me then? (Again, you're letting him know that it's very important that he "like" you, and that he should plan on using this as leverage to get what he wants in the future.)
Why do I want to pay and be nice when he is acting like he is? (The answer is obvious--you don't. That of course would be crazy)
He flew off the handle, cussing and swearing about how he can't deal with me, I cause all sorts of problems, etc. (Of course, he didn't get what he wants, so he's going to put on a good show for you. Might as well pop some popcorn and send in the Oscar nominations for best dramatic performance.)
After he rages, he apologizes and says he shouldn't have done that. (This is the repair phase, where he realizes he wasn't going to get any returns for his dramatic performance)
He then said that he was joking about the facepaint and that I am too emotional and take him seriously (this typically happens after he gets in trouble for saying something he shouldn't or that is rude). (In other words, he's putting it back on you--you cause me to be this way...in other words, he isn't apologizing, he's blaming his behavior on you in hopes that in the future you'll spare him the need to come up with elaborate debates and just give in and give him what he wants. He said he would never want to hurt me, so why would he intentionally say something that would upset me? I'm just too emotional according to him. I need to know that he would never hurt me.
He said that he will change when I change. That he acts the way that he does because I act the way that I do. (This is classic abuser talk. If you recast all the characters with paid actors, you already have a script for an after school special...)
I just get mad when he is so rude and disrespectful. (As you should! But what's probably happening is that he's pushing your buttons because he's gotten good at figuring out what they are.)
He said that because I am not happy, he is not happy and that is why he acts this way. (again, not taking responsibility and pushing it back on you. You can thank him for his "concern" about your happiness, but how he acts is more of a reflection on him, it's not about you...)
These conversations remind me of a new student I currently have (who I'm guessing based on the week we've spent together so far) is either ODD (oppositional defiance disordered), or has a personality disorder. Regardless of the reasons for his behavior, he has succeeded in alienating himself from nearly everyone in the class (because of the rude things he says), and has been trying to use a lot of these same moves on me (to see if any of them will work), but with no results. I'm assuming that he will either up the ante by being more defiant/rude or he will settle down eventually and see that he's not getting anywhere by being this way. We'll see. If he decides he needs to up the ante, he'll probably get himself kicked out of school, and then I'll never have a chance to try to help him. Either way, he doesn't get to run my class, or control my behavior. The main reason I'm telling you about him is that you can use a lot of the same moves I use in the classroom at home.
Scenario 1:
You ask your son to do something. He refuses. He then says something rude/inappropriate/emotionally manipulative in response hoping that you'll back down and he can get what he wants.
Non-compliance Strategy 1: I'm asking you to ____ now. (Repeat once if needed, but give them a minute or two and some space to choose to get with it. They usually will. If they cooperate, thank them for cooperating). (If the problem continues) Since you are unable to ____, the consequence is going to be ___. Do you understand?
Non-compliance with rude response: Strategy 2: You don't need to be rude. I'm asking you to ____ now. (Repeat once if needed). (If the problem continues) Since you are unable to ____, the consequence is going to be ___. Do you understand?
Non-compliance with rude/inappropriate response: Strategy 3: This conversation is over. Since you being rude to me, I can't talk to you now. Since you didn't ___, the consequence is going to be ___. (end the conversation. If he's still talking back, just reiterate "We're done now" or "we'll talk later" and walk away if need be.
Whatever you do, stick to whatever consequences you have in place for non-compliance, and enforce them with the dispassionate inevitability of Mt. Everest.
Scenario 2:
Your son asks you for something you aren't planning on giving to him. You say no. He then argues/whines/wheedles/cajoles, etc.
Strategy 1: I'm sorry you wanted ___, but I can't do that.
If the whining continues... Strategy 2: If you want ___, you will need to ____first. (if it's something he needs to earn or provide for himself, this is where you remind him of the procedures of how to do that.)
If the whining continues....Strategy 3: (If he's still bugging you about what he wants). I've told you that I'm not going to __. I'm not changing my mind. This conversation is over.
If the whining still continues: "We're done." and walk away.
Whatever you do, do NOT give in to the demands at a later time if you said no, unless your standards have been fully satisfied first. If you back down later, this will only create further incentive to escalate the behavior on future occasions.
All of this probably sounds highly scripted, but it works VERY WELL, even with really tough kids. The secret is that you leave out all of your emotional energy at the time, and become like a mountain--unmovable. Instead of getting sucked into the argument and allowing it to escalate further, you stick to stating what you expect. It removes all incentives for the kid to keep arguing because there's nowhere to go. They only get what they want if you get what you want. All the crying, screaming, arguing, name-calling, wheel-spinning etc, will not work. They can dig themselves into as deep of a hole as they want, but they will not get what they want until you get what you want. Once you get what you want, then the stand off is over. As soon as they've recovered feel free to reiterate that we all say and do dumb things sometimes, but you still love them, care about their success/happiness/etc. In cases where ugly things were said, you can follow up by reiterating that you don't appreciate rudeness, and that it's more effective to get what you want by asking for it in a civilized manner, and realizing that sometimes you can't get what you want, etc.
Hope this helps. These kinds of kids can be really hard to work with day in and day out, much less live with all the time. By they time they're teens, they've had years of practice of meeting their emotional needs through negative attention-seeking behaviors, and manipulative drama. It's a hard cycle to break. I don't know if they can even be cured of it, but at least you can train them not to use those moves on YOU. Best of luck!
Sageowl - your reply was amazing! It helped so much and made me smile.
I do want to say - I should have spelled out our situation better in the very first post. As far as the mother/friend thing. I was his mentor for 3 years before I was his mom. We did a lot together, talked, saw movies, went skateboarding. We were friends. I was his friend longer than I was his mother. And honestly - I know people feel I shouldn't be both, but for the most part it does work. He listens to my suggestions much better than I ever listened to my parents. His behavior and grades and social ability have increased tremendously. We are able to talk on a different level than other parents/children. It's just finding that medium that actually works.
LOVED the post. Especially about being mothers not friends. I tell my almost 16-year-old son regularly that my job is not to be his friend, but to be the grown-up in the room. One huge problem I see with a lot of parents today is that they are too busy trying to be their kids' pals instead of their parents. Be the adult folks,that's all I can say. (my picture by the way, is of my son with me a few years back...that's why he doesn't look 16 there)
Follow Mothering