I've spent the last couple of days working on a document that makes gear recommendations to Bike & Build riders. The main feedback I've gotten is, "you're just telling people to buy more expensive gear." My answer, unfortunately, is, "good gear is expensive."
Well manufactured bicycle parts have always been expensive, primarily because bicycling is such a specialty market. In the 1970s, you had to pay good money for brakes that worked going down a steep hill and high pressure clincher tires that would stay on your rim. While we've come a long way since then, I still don't believe that the very cheapest road bike available is suitable for a transcontinental trek.
In the procurement of bicycling gear, I think it is important for the first-time buyer to have an understanding of why different models of a particular item exist. There are several reasons that one part may cost more than the other: brand, material, weight, and durability are the first that come to mind. On a transcontinental tour, durability and material are paramount, and brand and weight are far less relevant. However, one must take care to not buy items of unusably or dangerously low quality!
In practice, this means that if you are buying a pair of bicycle shorts, you might want to take a look at that $150 pair of shorts, figure out what features it has that make it so expensive, figure out which of those features are the most important for your application, and then buy the cheapest shorts that have those features. The fanciest shorts will have lightweight fabric, flat seams, an anatomical chamois pad, and multiple panels. The most important feature here is the anatomical chamois pad, with flat seams being a second. Multiple panels and lightweight fabric are nice, but don't do as much to improve comfort if you don't have $150.
Of course, the quality of your componentry plays second fiddle to what is far and away the most important aspect of your gear: the way your bicycle fits. In the coming days, I'll post my thoughts on bicycle fit, with a practical "how to" guide for making sure that your bike really fits.
Stay tuned!