This didn’t work out, but it came close. Eventually I’ll figure out what material can replace the boot, at which point I’ll need to remember these steps…
That LED flashlight + laser pointer has a rubber boot over the push-on / push-off switch stem that makes it sorta-kinda waterproof. Although I wouldn’t trust it in more than a sprinkle, it’s my pocket flashlight and tends not to get soaked very often.
Anyhow, the rubber boot wore through:

Taking it apart, now that I know how, was easy enough:

Note that the mushroom part goes on the outside, which means the stem will vanish if the boot rips apart.
I planned to mold a boot from acrylic caulk, so I wrapped narrow strips of electrical tape to match the stem to the mushroom head, then wrapped a bit around that to make the final boot fit loosely:

A thin layer of oil served as mold release, over which I smoothed a blob of caulk. This looks awful, but the majority of the blob at the bottom will get trimmed off:

Unfortunately, the cured caulk turned out to be remarkably fragile. Each individual blob felt tough, but it’s really not designed to form thin membranes; I got about what I expected.
Pourable silicone rubber seems like the right hammer for the job: make an outer mold to surround this thing (or a 3D printed replica) and pour it on. I must get some of that, one of these days.
So I put the flashlight back together with the mushroom on the inside to keep the stem in place… and I generally avoid getting more than knee-deep in liquids, so not having a good seal won’t matter too much.