Brian,
You are brave to let this bunch look at your PSK. You have some good stuff! I too like to go to REI for my PSK collection. Let me get my Kevlar on and then I’ll add my $0.02 worth.
The rule of 3s: 3 minutes – die of lack of oxygen to the brain, 3 hours - die of hypothermia, 3 days – die of dehydration, 3 weeks - die of starvation. The idea is to meet your needs to stay alive and then do everything you can to signal so you will be rescued. Unless this is an EOWAWKI bug out kit?
My categories are: fire, first aid, food, navigation, shelter, signal, water, and weapons/tools.
Fire: dump the matches. A small lighter, ferro rod, and cotton balls are all you need.
First aid:
The most common injuries are cuts, scrapes, burns, and slivers.
REI burn gel (great stuff! I’ve used it on my boys), Band-Aids and triple antibiotic (good stuff!). Check out REIs small tweezers. The Imodium could save your life from becoming dehydrated. I would pick Benadril for the anti-histamine effect. I like Motrin for its anti-inflammatory effect. A packet of Purell can be a good thing.
Food:
Even a small fishing kit is overkill. A snack bar might be better.
Navigation:
Nice compass!
Shelter:
I see some cord. A Space Blanket or a folded up 55-gallon trash bag would be good. You can use the cord to tie some branches together to start some kind of shelter.
Signal:
You need a whistle, signal mirror, and a blinking light. I have a cut down REI Featherweight Mirror that I keep in my wallet. You need the Ritter PSP signal mirror or a real glass signal mirror. You might consider a Photon Freedom that will blink SOS. Also the Pretzl Zipka is a great LED light that blinks. A little roll of orange flagging tape would be good.
Water:
The Katadyn MP-1 tablets are perfect. The quart Ziploc bags are also perfect for collecting and treating the water. I hope you have a water bottle or something.
Weapons/Tools:
Great Benchmade knife! Why not throw a SAK Farmer in your pocket. It has a great saw and awl. REI duct tape – great stuff! Needle and dental floss – good. Safety pins – quick and easy repairs! A knife sharpener is a must!
I suspect your main concerns are going to be: treat any injuries, get warm and dry, and stay hydrated. Then you are going to want to create some kind of signals to get rescued.
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Thermo-regulate, hydrate and communicate.