Scarlett,
I'm brand new here but have been lurking for a while and have been reading this whole thread. I too have a "sensitive" child (although she's a girl so somehow that's okay :confused:).
I think your son sounds fabulous. Aren't boys supposed to be especially attached to their momma's? Is there some kind of detatchment with your DH's mom that makes him jealous when he sees his own son so attached to you? My husband is still a momma's boy, so he likes it when he see's that my son and I are close (but then again, he's only 4!)
I certainly agree with someone (sorry) who suggested that you try harder to pull out his exact concerns and then reflect those back to him. Classic sales technique! "So, it sounds like what you are concerned about is ..." and he goes "no, actually it's..." and you really get to the bottom of it.
I can tell you (not that this will help) but the reason we are homeschooling initially is BECAUSE my sensitive child was traumatized by the ps system. Children who are quiet, obey the rules and don't cause trouble, and are academically above average SLIP THROUGH THE CRACKS. My dd has developed a stutter from a traumatic public speaking thing in 1st grade. By 8 weeks into her 3rd grade year I approached her teacher to say - gee, I think this is really getting bad, what do I do? And she said "huh, I never noticed it..." This means this woman has not had a meaningful conversation - nor read-aloud time - with my child in 8 WEEKS! We pulled her out by Christmas break.
I just want to encourage you. Sensitive boys can be a threat to a certain kind of man, but as a woman married to one for 20 years, they are a blessing to their wife. I hope he does not squash that personality!