You should air down anytime you're going to hit a trail. Standard dirt or gravel road, no, but actual trails, yes.I used to carry a 60+ lb backpack, it's now 35. Over time I realized I didn't need the extra weight. Some of that came from experience, and some of it came from others with more experience explaining how to do it better.
Relatively speaking my off-road confidence is about where I was at 55 lb backpack. Still learning and leaning on the others in the group. (Never wheel alone) I'm starting to build an effective kit. For example, I've not needed my air compressor but others in my groups have.
Everyone needs their own compressor of some kind. If you run 33" tires or larger, it takes forever to air up and compressors run hot quickly.
I also don't take the entire kit everywhere I go; no need. However, I generally don't just bring my kit for me, but to help others. You'd be surprised at the simple looking stuff people can get stuck in particularly if it's been wet.
My kit also isn't all that heavy or extreme. tools and shovel go everywhere along with the Maxtrax. I also prefer soft shackles and don't normally travel with bow.
It's ok to have folks in your group specialize in stuff, but everyone needs to be able to recover their own vehicle. I don't wheel with guys with no gear.
Keep learning, plan, and spot where your wheels go by walking trails ahead first; that'll get you stuck far less.
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