The right answer is "it depends," a lawyer's best answer to almost any general question, because it is true. Having the best gear won't substitute for skill if you don't know how to use it or get yourself in a situation where even the best gear won't help. Putting up a $500 tent in the wrong place may not not have the same consequences as putting up a $100 tent, but it depends on where that place is.

Having the best clothes won't save you if you are lost or run out of food. Winter campers who go out without checking the weather may find themselves in trouble, not matter what they have with them. The same is true of climbers.

I consider myself a beginner winter camper. I make up for my lack of skill by taking along a very sturdy four season tent, enough clothes for far worse weather than I expect and don't go so far out that I am miles away from an exit strategy if things go really wrong. I have enough with me that if I got trapped in a storm, I could stay for a few extra days. I have either skis or snowshoes and a shovel-the basics needed to travel.

I don't consider much of my gear to be "the best," but it is more than adequate for what I am doing. I think some of the skill is in knowing what to take.

When I used to teach scuba diving (which I bring up every now and then), one of the most important things I could teach someone was this - know how and where to get out of the water before you get in. Any idiot can jump in anywhere with gear on; it is knowing how to get out that saves you.
_________________________
Don't get me started, you know how I get.