In Wired Magazine's most recent edition, they mixed up their gear reviews approach. Rather than simply splashing a bunch of products on a page and rating them, they sent correspondents out on adventures with the gear and asked them to report in. I can't find the article online, though I can find part of the review of the first adventure here. These reviews turned out to be very instructive, though almost certainly not in the way Wired intended them to be.
Wired sent 4 folks out on solo trips: one on a high-end motorcycle, another on a fancy bike, another in a canoe full of gear and finally a brave sole on a super high end stand-up-paddle board. By most measures, all four trips were a bust. To the credit of the adventurees, they reported back their experiences in all their mistake-filled glory, rather than fudge the trip reports to make them look like the iconic trips that were supposed to be.
Now I know that outdoor trips rarely go as planned; that room for failure is one of things that makes heading into the wilderness so much fun. But there was definitely a theme among these trip goofs: good gear, awesome gear in fact, can't replace familiarity. Sure, that high end motorcycle may be awesome, but that fact won't don't you much good when you realize the bike is too large and too overloaded. And sure, that may be a super high end bicycle, but the fact the sizing goof made it incompatible with the trailer you were planning to pull, goes a long way towards undoing all that awesomeness. And the fact that the stand-up-paddle board has a motor is great, until you realize you forgot the ignition switch at home, leaving it as little more than an expensive and very heavy paperweight.
Of course, these were intended as gear reviews, so the fact that the reviewers had some rough scrapes is to be expected. But, it's a mighty important lesson to take with you when doing trip planning: blindingly trusting in gear because it's top of the line is almost certainly a bad idea. Better to test out gear on smaller trips, and phase items in a little at a time, rather than just assuming shiny-and-new equals better.
I've actually fallen for this trap before. Last year, we did a short backpacking trip and I opted to carry my brother's Canon Point and shoot rather than either my cell phone camera or DSLR. I'd assumed that the zoom lens and various camera features would be preferred over my limited cell phone. Turned out, I was way out of practice with small Point and Shoot cameras. I had forgotten how painful the shutter lag is (even though it's only a couple of seconds, my cell phone and DSLR are basically instant) and all those camera modes turned out be just downright confusing. Sure, the camera had a super long zoom, but many of the photos came out shaky because of non-optimal settings. This was an important reminder: gear that tested and trusted beats out an impressive list of features any day.