The latest gear isn't important to enjoy a trip. It does nothing to offset inexperience.

But as a gear head, I find that new toys are fun to play with. I like stoves and fishing gear - I have duplicate stove sets - but that comes in handy outfitting newbies with loaners. I have several shelters but they each are best suited trips to different environments, or different seasons, and the same with backpacks - having a separate pack for SAR is sort of important since you have to go at a moment's notice, and some of my gear has to be stored in it.

And buying a down sleeping quilt was the best investment I've made, since the cycle of cheap bags was ridiculous - no sub-$100 bag will ever replace a good high quality down sleeping solution, in terms of lightness and warmth. Never going back to cheap sleeping gear.