Great thread and it's so true. The desire to get after 'em is what's important, along with physical fitness and sharpening your skills.
My first real elk hunt in CO ten years ago found me in a Coleman tent with screen windows at 11,000 ft in mid October with two feet of snow on the ground. I was wearing old Rocky boots and cotton socks, along with cotton everything else. It was miserable, I could hardly sleep at night and hiking during the day was brutal.
Over the years I've slowly replaced gear as I could afford it but still don't have everything I want. Finally bought a Kifaru pack this year after 8 years of using a Black's Creek Alaskan pack (which packed out multiple elk just fine but started to fall apart). My goat tag in 2012 forced me to pony up and get some real mountain boots. I've got a few pieces of Sitka and wool base layers now. I still can't justify buying a new jacket though, my waterproof Redhead jacket works just fine for $100.
I'm still using my grandpa's old .308 lever action, no reason to replace a good all around rifle and I'm sure he'd be happy knowing I use it. I did put a better scope on it though.