I think you need to be prepared for anything, but be prepared well for what you can anticipate.

I had the Doug Ritter PSK for about a year now. I have never used anything in it, but try to keep it around as the back-up for the unexpected.

This weekend I am going camping. I will have the PSK in one of my pockets and I always carry a pocket knife and Photon II light. Since I will be in the woods all weekend and since it is winter, I will have an extra windbreaker and a poncho in my day pack along with gloves, chap stick, bic lighter, matches, para cord, multitool, some food, water purification tablets, water bottle, a good compass, map, flashlight, knife, small first aid kit and toilet paper (just to mention a few things).

Last summer, I went with the wife and kids to Washington DC and did the typical tourist stuff. I wore a small day pack with the PSK in one of the inside pockets. I had a windbreaker/rainjacket, first aid kit, water bottle, guide book and maps, granola bars and a few other odds and ends. I did not include the fixed blade knife or multitool. We had to go through metal detectors/security checks a few times at the Smithsonian but had no problems with a pack that contained basic tourist looking stuff. About the middle of the day in DC with the kids the Tylanol from the first aid kit and water bottle really came in handy. Also, the compass was nice to have a few times.

Just my opinion, but I think you need to have your small basic kit that goes everywhere and that you keep intact, then build around it depending on where you are going.