some well engineered equipment will have features such as ease of set-up or being properly water proof and breathable or easy to light or fast to get into. These features may make it a lot easier for someone new to do things properly, and may stand up to worse weather than cheaper gear, but one still needs basic camping sense like not setting up that nice Hillberg tent under a dead snag in a wind storm. And you still need to know how to light a fire. That said, there are many places in Oregon where you cannot light a fire without a chainsaw and an axe, and the only wood might be about 8 feet in diameter at the base.
Whether skill can make up for a lack of equipment is kind of a balancing act kind of question, but those who are highly skilled and resourceful can go where others cannot. An unskilled person may benefit greatly from having good gear, but good gear cannot teach you how to use it.
Jim