I don't really understand the OP. Its a great list, but was it intended to be what you would start over with knowing what you know now? Or just a good economical way to cover your bases and you might trade up later?
Knowing what I know now and if I had to replace this would be what I would go for:
1) Hammock (probably get a Hennessey again because it comes with tarp, but I have my eye on a Warbonnett now since I have an extra tarp already). Won't bother with a tent again. A supplemental purchase of a larger 8 x 10' tarp is useful for additional privacy and to use a winter tarp.
2) Sleeping bag - my most versatile bag is this cheap (I bought it for about $60 in 1998) Woods thinsult barrel bag. Its rated to 32oF although that is a bit optimistic. Compresses to the size of about 2 water bottles. Great bag for 3 season. Not good for late fall or winter. Winter is a whole different deal and different list! Lessons learned - I later bought a much nicer $150 synthetic bag at -12oC for extended use. I really don't use it that much. Its too hot for warm weather and isn't warm enough for the real cold.
3) Wool blanket, I buy one again just to help extend the sleeping bag during car camping in cooler weather and because they are nice to have. I think a wool blanket beats a poncho liner, albeit I'm interested in a Kifaru some day.
4) Thermarest - wayback in 96 or so I bought one of the ultralight thermarest pads. It has a lower R-value than the full sized ones, but you can compensate the comfort factor by blowing more air beyond what it 'self-inflates' to. I've used this for pad for almost 15 years and never regretted its purchase. In winter, I supplement it with a foam pad under the thermarest.
5) Cookset - Trangia 27 series with mini-kettle. Best cookset/stove combo I ever had and costed less then my MSR whisperlight without the cookset.
6) Noteworthy addition - twig stove, I initially made mine out of a coffee can. Later upgraded to the Ikea stainless steel cannister courtesy of B. Andrews. Worthwhile replacing!
7) GSI Stainless steel cup, the one that nests a 1 L nalgene container. Great piece of kit for cooking and as a mug. Personally, I still like the cup/nalgene better than canteen/canteen cup, although the later can be had cheaper. I have the $25 goyot stainless steel bottle and would not pay to replace it. I like cooking with a cook kit better.
8) MSR waterfilter. Fits to a widemouth nalgene thus integrates with 6. Love this and would buy it again. Also include backup chlorine dioxide tablets.
9) Backpack - I really like my maxpedition falcon II quite a bit. But if I had to buy just one pack, then I would get a 50 L bag from one of the suppliers like MEC or REI. I have a Sierra design bag with internal frame that is more versatile under multi-day camping trips then the maxpedition. If you have to start tying crap to your molle bags then you are over stuffing them.
9) Knife - oh god, there are so many to choose from. Knowing what I know now? I'd contact Brian Andrews and ask him to make me the Terrasaur model but with a convex edge. I might also consider BRK&T Aurora. I might still be tempted to just mortgage the house and buy a Rick version of the bushcrafter. Lessons learned. I still don't like a mora after owning two of them. I have one of the newer ones now but I don't like it. I don't like big chopper knives. I don't like skeletal neck knives. I like knives that are 4-5". I don't adore scandi's, but I do sort of like them....I still like convex more though. Chances are, very likely, if I had to do it again and knowing what I know now...I'd still end up with about 5 knives.
10) Folder - hands down I'd get the OHT-SAK. I just ordered a second one as a spare. I also ordered a custom leather sheath for it with a firesteel loop. Now, I think I'll like a firesteel loop along side of my sak, both within easy reach on my belt, much better then the pocket pool thing.
11) Chopper - axe would be king for me. I'd probably go for a 25" GB Scandinavian forest axe. Thats a pretty versatile size for wood prep and if I don't want to lug it then I'll leave it at home. Right now I want a big'un axe for winter - 35" handle. I'm pretty happy with my B. Andrews modified Snow and Neely, but Brian doesn't work them anymore and he said the FF of S&N has tanked. So I won't look to replace it.
12) Saw - I really like my Swedish takedown saw - the trailblazer. The next time, I'd go for the 23" blade instead of the 18" that I have. Since my SAK has a small saw that covers all my needs for small (1-2") pieces of wood. A full size buck saw is amazing to have in the bush for serious wood processing especially when paired with an axe.
13) Navigation. I'd stick with my Suunto A-30 compass with N. Hemisphere balanced needle. It has great features including glowing bezel that takes a solid charge. I prefer a baseplate compass to a sighting one. I would still probably buy a cheap GPS unit. I would get the cheapest garmen, e.g. etrex. I'd use it just to mark my entrance, camp and then shut it down. Use for emergency tracking back home. I don't really heavily on GPS (almost never use it), but they are a good backup if used properly.
That would be the gear list. Cloths/boots would be a whole different matter and I'm too tired to think that out.