So I will attempt to answer several questions in this post...

#1 My current bag is a 20 degree bag, although I never get the full warmth capabilities out of it because i use it more like a blanket

#2. My "trail kitchen" looks like this:
JetBoil 13.70oz
Fuel Canister 7.10oz
Stainless Steel Mug 7.65oz
Titanium Spork 0.30oz

Typical breakfast = 2 oatmeal packets and a satchet of instant coffee
Dinner is usually a Mountain House meal
I seldom eat lunch on the trail, i just nosh on homemade GORP throughout the day

#3 My budget for a sleeping pad is $150. My budget for a tent is probably around $300. I might consider going slightly over budget if I fell in love with something...

#4 I purchased a small digital scale and weighed pretty much everything I pack...except for the food (I will start doing that)

2 things I KNOW I did wrong on this trip. 1 - I packed too much water (4 liters). Considering I brought 2 filters with me, that was overkill. Although the gentleman I met on top of one of the mountains had a dog that was thoroughly grateful for one of those liters...he was a cute dog, so it was worth it! 2 - I packed too much clothing. I tried to pack for worst case scenario, but brought probably a pound's worth of clothing that was not necessary.

If I shave off the 2 liters of water and clothing alone, that is approximatey 5.4 pounds off pack weight (the water killed me). However, this is based on 2 hikers sharing communal weight. If I carried all the necessities, I would still have some weight-saving to do.

Based on the responses so far (thank you very much, btw), I will set my sights on a new shelter (notice I didn't just say tent).

Between better fitness levels, a lighter pack and better decision making, I will be putting more miles between the TH and camp. Thanks!