I'll be curt since we know each other.
So it is personal preference but since you are planning on taking rain pants why not drop the shorts and boxers and pick up some running shorts w/ a liner. Would let you drop belt, boxer, boxer2, shorts for just one 5 oz pair of shorts.
In Oregon I discovered Crystal Light Energy as a caffeine source. Forced me to drink a liter to get the caffeine and in my head helps counteract the diuretic effects.
You probably already have them but... Darn Tough is definitely a brand I'd recommend I, however, do not like cushion socks. It's simply extra material that really doesn't "cushion" (just feels plush) and soaks up more dirt and water than a thin sock would.
You can use my homemade poles if you'd like - 3.5 oz per pole. They are fixed length which might add a learning curve to setting up your shelter.
I'd recommend adding super glue, safety pins, needle and thread and a bandana as gear repair/first aid.
Your tooth brush weight is high, cut off that handle. Bolt cutters work pretty well.
Sawatch + bivy is going to be really warm. Try it out but I find bivies too stuffy and prefer the poly ground cloth. I also noticed (unless I missed it) you didn't have a hat for warmth or sun on there - might be something worth taking. Oh, and if your using a liner bag you really don't need an additional stuff sack for your quilt.
I would say "Wait for one of the sales and pick up a Jam at GoLite" but I don't think it would even be a weight savings these days.
And truthfully, you won't need maps for the CT proper, it's really well marked. If you decide to do alternate routes -- which I highly recommend the CDT from Twin lakes -> Monarch pass and even a little past until it joins the CT -- take some maps the CDT is moderately marked once off the CT. They're adding that stretch as an "Inner Loop" to the CT so don't you worry about it counting as a thru! There are also a couple pretty easy fording short cuts you can nip instead of walking a mile to a bridge to turn around and walk back (like Twin Lakes) if you have a map.
Edit: You don't need an insulation jacket - I was just fine with windshirt and a quilt.
Should of said "attempt to be curt"