I understand what the OP is saying about not liking the DSS, but she really means his behavior. I'm sure she loves him just as much, but loving someone is different from liking how they act. (((OP)))
I'm not trying to start a fight here, but I'm really intrigued by the people who posted from the school-hater side of the fence. You've said that you found your niche and are doing well, but do you think you've become achievers? Do your families think that you've turned around? Or have you just kept your low standards and your families have accepted it because it's unchangeable?
I ask because I went to school with a cousin in just this situation, except that he transferred to my school after he failed several courses at an elite high school. He goofed off throughout high school, did some community college work and is a journeyman. He's happy, but he's never really ACHIEVED anything other than satisfying himself and getting by without really screwing up. Don't get me wrong: I love him, but I do feel that he's capable of much more. Whenever his name comes up, there's an air of regret, of lost opportunity, that surfaces. He's sort of "dismissed" with a "Hey, he's not on drugs, he's never been arrested, he works here and there, and he isn't hurting anyone."
I often think of a former coworker who had a law degree, a masters in business technology, and an insurance license. She worked in the IT department of a major insurance firm, handling the contract-development projects. That's a real niche, with achievement on top.
In Grade 5, I had a whole bunch of testing done because I was failing school. My IQ came back ridiculously high - like much, much higher than anything anyone had ever seen before.
I happily underachieved almost all the way through high school and squeaked by with summer school (which was free in our district). I put the effort in and got the grades only because it meant I could skip a year and get out early. Then I dropped out of university.
Eventually my boyfriend (now my husband) convinced me I needed to finish my degree, just to say it was done, so I went back and took only fun, interesting courses and ended up on the deans list without ever intending to be there.
What have I achieved?
I have a solid marriage and two great kids. My husband is my best friend!
I homeschooled my children during the early years, and they both have a really good grasp of the basics - reading, writing and arithmetic. I'm proud of that!
I'm currently teaching Grade 7 math to a friends son, because he just dropped out of school and his mother doesn't want him to go through life without knowing his math.
I painted a mural on my bathroom wall.

More murals to come in the rest of the house...
I painted murals in the local elementary school.
I have an article published in an encyclopedia.
I illustrated scholarly books.
I wrote a novel over a three day weekend, and won third place in a contest!
I put my husband on a diet and he lost 65 lbs, and now the doctor says he doesn't have to be on blood pressure meds after all.

(I'm very, very proud of this one!)
I figured out what was medically wrong with my son, and what had to be done to help him.
I nursed my elderly cat through the last days of her life, and used this time to teach the kids about life, aging and dying.
I computerized the entire membership database of a provincial non-profit organization, and co-ordinated for them for several years after.
I've taught First Grade Sunday School - and I've also taught sex-ed to fifth graders!
I've been a field captain for a local charity for several years, and I still volunteer in at least four other charities.
I've knitted blankets galore, and made socks for everyone in the family. I've donated some of my work to charities.
I've designed websites, and graphics for my friends.
I may not have earned much money in my life (okay, none), but I'm definitely proud of what I've achieved.
***I do NOT feel like an underachiever, and I would be very annoyed if my family looked at me with "an air of regret, of missed opportunity".