Everyone has their own approach.

I currently have 3 PSKs, one for EDC (suburban, currently), one for the woods and a third for on the water (sailing). They're all small enough to slip in a pocket. Of course there is more gear in my vehicle, in packs, in my desk at work, in the boat, whatever.

For me, the PSK is intended to be a last-ditch backup only, never a set of primary tools. I've been known to take day hikes, up to say 11 miles or so, with just what's in my pockets, but around here, 5 miles down the trail is most often less than a mile out in some other direction, and there are other hikers, and cell phones, park rangers, roads, campgrounds- a literal "walk in the park", generally. You'd be hard pressed to get yourself in real trouble. I've had sudden, unexpected weather many times, and failures of footgear, found out the water I packed wasn't potable once, and been a mite disoriented once or twice, but I've certainly never had to bother the rangers.

On the other hand, in more rugged terrain, I might well have an emergency bivvy kit in a day pack for a 3- mile walk... certainly some sort of foul-weather gear and insulation if it's cool, in addition to the PSK. I guess I just tend to pack the minimum I think necessary for a near-worst-case scenario, like breaking an ankle at the furthest point in the hike.

On those more ambitious trips, or across water, I think everything in the PSK is, or should be, just a backup for some other piece of equipment, and usually the second backup... the minimum that I don't want to be without if I'm separated from my pack, can't get back to my vehicle, or office- I can't get to my primary gear.

Personally, I'd consider any time I really have to "raid" the PSK in non-life-threatening situation a failure to prepare properly otherwise. Nothing to beat myself up about, but a clear message that I did something wrong. It's not for routine use.