Nah - you don't need to spend that money every year.
The pack should buy new neckerchiefs for every scout. Make it part of the program. Add in $10 to the dues at the beginning of the year. Don't require the hat. Each den should make their own neckerchief slides.
The scouts buy one belt buckle when they start cubs, one when they get the tan uniform.
I think there's a bunch of steps that can happen here before you start calling district and council folks.
As has already been shared - talk with the Scoutmaster. There's about a 95% chance that's all it will take. The conversation is simply one of "my son's going to have a hard time advancing if he has to write out these worksheets." Just about every Scoutmaster I know would say "well, then let's find another way".
If the Scoutmaster doesn't work out, then you call the Committee Chair. The Scoutmaster serves as the discretion of the Committee. The chair of the Committee has a lot of sway as a result.
If that doesn't work, then you call the Chartered Organization Rep. You explain how their Scout program is making it hard on your special needs son to advance.
At that point, if I couldn't find a way to make it work, I'd do one of two things.
1) act as transcriber and write out the forms.
2) call the troop down the street and ask when their meeting is. If after all that, you couldn't get it sorted out, then I wonder what kind of troop this really is.