Hi JBDad - Try not to get too discouraged. I see some positives in your post. You and DW knew before school started what troubles might occur, you sought and got a grade skip, and you recognized when your son wasn't getting the right academics. You have been very successful in your advocating thus far, and hopefully this streak will continue.
I think there has to be a certain amount of time when your HG is in school before you can really find out the specifics of what your child needs (a control group phase?). It is helpful that you got such tangible results from bringing out the higher math workbooks. This is a great example to bring in to the school. Perhaps they will ultimately decide that another skip would indeed be easier for them (it can't hurt to bring up the possibility of a skip mid-year, like Cathy's DS did).