Can good equipment replace skill? No. It simply means that your heirs will inherit lots of good stuff - which they probably won't know how to use, either.

I backpack in areas that are, by some of your standards, heavily crowded. I see all kinds of gear, from the cigarette premium stuff to low-end stuff from Dick's or Dunham's to REI brands to high-end and, on the sunny, pleasant weekends, everyone's having a great time with whatever gear they have. But let the weather turn, and I start seeing the low-end stuff abandoned in campsites or beside the trail, thoroughly trashed. It wasn't always because the gear failed, it's usually because the people using it didn't know how to get the most out of it. Usually, when I run across them a mile or so later, huddled under a rock shelter, I notice that their "rain gear" consisted of a cotton-lined, uncoated-nylon, company-logo windbreaker layered over cotton sweatsuits.

On the other hand, I have seen (and been one of) the people who were warm, dry, and happy using lower-end gear in foul conditions. But we knew the limitations: we didn't put our fiberglass-poled Gander Mountain tent out on the ridge in 40 mph winds; we tucked it off the ridge, in some trees (after checking for widowmakers), with some bushes as a windbreak, if possible. We knew that a coated nylon poncho was still better than a sweatsuit in the rain.

Now, one observation that goes along with this is that, in many cases, experience drives a hiker to choosing better quality gear as ( and if) they can afford it. They know that a good, high-end tent will have design features that will simply make it easier to deal with foul conditions. Of course, you still need the know-how to use those features. But generally, I've found that the more experienced folks are using the better gear, and that the newbies with a minimal collection of better gear are often being mentored by those with more experience.