First of all you're being too hard on yourself.
over the past year or so i feel like he's regressing... he's really acting like a 3yr old... he's now clinging to stuffed animals that he never had an interest in before... he can't sleep alone anymore... he's way too dependent on mommy... and now he's starting to say things like "i hate my life" and "i'm just waiting to go to heaven"
This sounds like he is suffering from Depression and Anxiety (if not a severe case of both), which people ride off as bad behavior in young kids.
Yes Young kids and toddlers can suffer from depression and Anxiety, but again it normally gets labeled as bad behavior
You should take him to his pediatrician and have him tested for both.
Then consider going to a therapist before dealing in medication.
I started getting depression at age 8 or 9...
I've had anxiety and OCD for as long as I can remember....
If I was treated and diagnosed in elementary school, I would have done a lot better in life...
Don't fret, there is plenty of help and programs for kids suffering from AS and other stuff than there was 10 years ago.
People with Asperger Syndrome have a higher chance of getting mental illness with it, including depression, anxiety, OCD and even severe forms of mental health.
Human males have a vastly higher chance and rate for mental illness than their female counterparts
Human males from the time they start puberty to 30-35 are at very high risk of developing mental illness, once us males pass 35 our risk factor for mental health issues fails in line with women.
No one knows why this is...
He like many people Asperger Syndrome, may never bond with his peers and/or never form a healthy bond with anyone.
He can still make successful life for himself without bonding with others.
The rest of it just sounds like a 9 year old being a 9 year old and coming into their own.
I think you have forgotten what it is to be 9 (start of tween years).
I bet if you talked to your parents, they'd tell you how you complained about life and school being unfair, talking about hating life, not wanting to sit still, and fighting the rules...
They will also tell you how bored you claimed to be and how nothing they did worked.
Hell this sounds like all most of my cousins and all of my sisters at that age.
You need to work with your son to find the structure and routine that works for him, instead of imposing what you want on him (this goes for all kids). Also being strict rarely works out well, as does being lax... You need to find the proper balance.
You also need to keep to what you say and hold the line. It's not easy, but your son will take you more seriously in the future (this goes for all people).
Also you need to including the Teachers into this mix, since they have him during school hours.
They can give you information on his social behavior and what's going on.
They can also help as well...
Everyone who important in his life has to be included, every part of life is interconnected.
This comes from someone who grew up with all as undiagnosed Aspie...