I think it's most important to know the limits of your gear to know when you need to be extra careful in using it, or when to bail out.

However, some of what you're talking about is also "experience" - anyone heading for WCT without a small tarp is asking to be uncomfortable

I am reminded very much of a rockwall trip a number of years ago. I was hammocking, packing a 30 litre pack with my blue foam on the outside, and had everything I figured I needed.

Hiking the same direction were two young guys with enormous packs, a bombproof tent, sausages, glass jars of peanut butter, etc.

On day three in numa, It's rainy and cold, I rig my hammock under my hammock tarp, then get out my siltarp and rig it over the campsite bench. I pull some avalanche debris that's dry and breakable from the stream and make a fire in the pit, and have my soup. I'm soon surrounded by the guys, and another group from the campsite who:

1) were hiding in their tents because they didn't have a tarp.
2) Couldn't make a fire because they "didn't have an axe or saw".

Oh well, they were at least pleasant company.

I think it's less about the gear itself, than about the knowledge of how to deal with unpleasant conditions without simply hiding and being miserable.