I wouldn't even carry half the stuff people consider necessary. It is always a planned event. Yep already been out there and dropped stuff off! It is also a part of scouting too. Good luck to the person who doesn't plan. Why in the heck would a guy want to try to take everything with him and the end up with nothing. I guarantee you the only correct way is to have a small string of Hotel Hiltons along the way. Start planning your deep woods excursion today or go all willy nilly and regret it.
the most important part of new gear is to use it pre-season on short trips to make sure it works the way you want and does not malfunction. I use these trips all season and always bring some new toy with me. spring is a good time to test new shelters because of the thunder storms that pass through the high country. I go out early winter to test shelters and bags in the cold weather and weight of snow on my shelters. I often take new stoves up when there are high wind warnings to see how they work in high wind and so on and so forth. Test your gear as often as possible so you know it will work, know how to use it and know what works best under what conditions.
This was mentioned on another thread started by Tikkamike a few days ago, but I thought I might mention it here as well as folks checking out this thread might benefit from this emergency bivvy if they haven't seen it:
It really is half the size of a soup can. No kidding. At 3.8 oz and $13 in the link above and as small as it is, it's probably a reasonable thing to pack if you don't always have your tent/bivvy and sleeping bag with you when you hunt.
I've been packing one of those on all my dayhunts for several years. The one time I used it condensation buildup was bad inside it, but I stayed warm which was the important thing. I've been packing that bivy, a kifaru paratarp, and a cheap mylar blanket. The cheap mylar blanket isn't much good as a blanket but can make a huge difference when used as a reflector for a fire.