Always up for a beer, it would be great if Jason could join us too. As for your list, clothing is tough to figure out here. I have been experimenting with different layers all winter on day hikes and nightly dog walks, just to figure out what keeps me warm while moving and stopped in various weather.
I think if you swap out your fleece for a wool hoodie or Patagonia R1 Hoodie and add a light down jacket (preferably with hood) and a lightweight wind shirt you would be fine for most conditions. The hoodies will keep your head warm when using the quilt and work better on the trail than stopping to put your hat on.
Just varying your baselayer, (heavy or Light) has a lot to do with warmth as well. Then just experiment with rain gear etc. as time goes on you will learn what you do not need. I am still trying to figure it out myself, I have only lived here a year and just found this site a few months ago, it has been really helpful, especially the technique articles.
As for dropping major weight, your backpack will be the big bang for the buck, just buy something a little on the big (but light) side so you have room when the kids come along (65L?). I do not know how warm the Big Agnes pad is but a Thermarest prolite is warm and comfy, a short is 11 ounces. You probably bought the rainshadow for when kids come along, which is fine, there is always a compromise.
Allen Butts had his Colorado Trail gear list on here not to long ago.
Anytime you want to head out for a quick over-nighter let me know, i just went out last night.