I didn't have the funds to buy the best stuff. There are some great, lightwieght, durable equipment but much of it was beyond my budget. Learning painful lessons sucks, but I can tell you I got a high quality pack after one real trip. It took two trips to get a lighter sleeping bag that was good for cold weather.
I am still trying different combinations of clothes and such but only carry dried foods now. I tried different foods, cooking, tents, and have decided the next big change will be a quality tent. Saving wieght becomes a difference in how well you feel after a day of hiking.
My first week trip into wilderness I was carrying over 60#. My next trip was with a much better pack. I carried about ten pounds less, and was much better off due to the proper fitting pack.
It's a learning process I think. If you have experienced packing friends I'd ask them to help you set up, and go with them on several short trips first.
This sounds just about the same as my learning curve, and I am glad it's done with. Good advice to slowly accumulate lightweight quality gear because not many can afford to buy it all at once.
If I was to list the items I'd concentrate on first, as far as getting quality stuff, boots would be at the top of the list, including socks that work with the boots and footbeds/arch supports as necessary.
Then, a good, lightweight pack that's built to carry heavy loads and fits my particular body type. I really like my Paradox pack, but there are lots of good options.
Then, focus on the "big three" in terms of your heaviest items: tent, sleeping bag, and pad. I like lightweight floorless tarp-style tents with plenty of room for gear, like a Go-lite SL-5 for two people, or the shelters made by Seek Outside. You'll need a light ground sheet for your pad/bag, and a piece of Tyvek works well.
For a bag, I've used a Marmot Helium 15 degree bag with good results, but I hunt mostly in September so 15 degrees is plenty. Get a bag rated to zero for later hunts in the mtns.
For a pad, I'm using a Thermarest Neoair right now, very light and compact. Also, the Prolite series is good but not as light or compact.
It goes without saying that you'll need a good windproof waterproof shell, that's another significant investment. I've been happy with a set of Marmot Precip, I really like the full-zip legs for putting on over boots. Add a good pair of quiet gaiters too.
Focus on those first as far as quality/lightweight gear and that's where you'll get the most weight savings.