A while back, I was visiting with a young aviator, who found out I'd flown commercially in Alaska for a number of years. He commented that I must have done a lot of "really scary" things, flying there.
I thought about that for a moment, in the context of all the "STOL this and that" that we are bombarded with via the internet these days, and responded that, in the contrary, most commercial operators in the bush DO NOT do a lot of "really scary" things on a day to day basis.
That said, to the uninitiated, and to the newby, a lot of the things done out "there" LOOK pretty scary. And, yes, occasionally, as you noted, sometimes a bit of doubt slides in there.
Those ops often look marginal to the uninitiated, but they are generally done in very calculated fashion, and based on a good bit of experience, recency and skill. But, in a "STOL competition", if a competitor yanks on full flaps just a hair too soon on a takeoff, the worst that happens is, they scratch.....no harm, no foul.
But, the bush operator to makes the same error, at a point where he or she REALLY needs that little extra boost, may wreck the plane. So, a lot of calculation goes into that kind of operation. Break your plane, you may spend a night or two in the boonies, and you may be out of work for a while, maybe a long while.
But, you are doing exactly what you need to do.....look at every one of those situations where things were a little "close", trying to assess what you did wrong, and how you could have done better. That really helps the learning curve, and over time, you become more and more precise and proficient, both in the pure flying skills, but also in your judgement of where to go somewhere, and precisely the conditions you need to make it work. With that experience and knowledge, now it's easier to say NO when it's necessary.
I am reminded of a small oxbow waterbody that I used to work crews in and out of. A Cessna 185 (and later a 206) with two people and all their camping gear and sampling gear. That short, narrow oxbow had a serious curve to it, and trees both sides. The wind had to be "just so" to get OUT of there safely with a load, though getting in was pretty easy.
More than a few times, I arrived overhead, didn't like what I saw, told the crew on the radio that I'd be back after midnight, hopped over to a cabin 20 miles away, took a nap, and returned when the wind had laid down. That was based on trying to come out of there with a crew early in my experience there when the wind was wrong. Popped up above the trees and nearly got slung into the trees opposite by the rotor..... Didn't break anything, but learned an important lesson by getting waaaaay too close.
Just like you're doing now. Good for you!!
Mike