Jason,
That is one of the problem with kits that don't stay on the person. As you mentioned when your bottle PSK was strapped to your boat; if you had lost your boat you were left with what was in your pockets and on your person.
That is my main problem with the whole bottle PSK thing. You have to at least strap it to your belt or something and you may be tempted to remove it.

In some ways I have begun to believe that some PSK's are too large and have too many things in them making them prohibitive to carry. Even the small pocket sized kits can be too big in some cases.
One example is trail running. I run in the local East Bay parks; they are quite wild for being in the Bay Area but most of the time I am on trails that I am familiar with are easily followed. None the less I still like to have some emergancy gear but I can't put a PSK even one as small as Doug's PSP in my pockets and I don't want to carry a pack. So I clip a Mini-Grip in my waistband and I put a Photon, mini Bic and whistle in the tiny pocket on my shirt or shorts. In cool weather I carry a very light windshell but in summer no jacket. This is about all I could stand to carry when only going out for an hour run. Point being that sometimes all you really need are some basics and knowledge because to carry more might not be appropriate. In a bad situation I might wish I had more gear but in the case of an hour trail run how much more can you carry before it inhibits your running?