I work at a large aviation university, and I have noticed this same thing with a ton of our other instructors. We have very tight rules regarding everything weather related. However, I have found that I can go to the chief pilots and get approval to fly in almost anything (as long as it's not into icing conditions). 30 degree crosswinds at 24-29 kts, last week visibility 2sm BR/HZ for most of the week, and many others I have gotten approval for. There are only one or two other instructors who even tried to get their flights approved. Most of the others just didn't even try. Getting a Special VFR clearance, getting clear to do maneuvers, then getting a pop-up IFR clearance to shoot multiple apporaches back in is really not difficult.
That being said, when I first started I was nervous about not letting my students take mistakes too far. After a few hundred hours of dual given, and slowly letting them make more and more mistakes, it really takes a lot now before I will step in. 9 times out of 10 I don't even need to fully take the controls. Most of the time I just apply the correct inputs, and the student instantly realizes their mistake. However, I do have one commercial student whose first instructor would yell at him for any simple mistake. In fact, his instructor wouldn't even let him park the airplane. Our first flight together, we were taxiing in, he stopped on the ramp and tried to give me controls. It took a little convincing, but he finally picked a spot and went. I've been working with him for about six months, and he has gotten better, but when weird things start happening, he shuts down and no matter what I do, he just hands the airplane off. It's sad to see, but I am going to get him out of this.
Remember our job is to pass our own knowledge and experience to others. If someone doesn't have that experience, it's hard to pass it on. I have done "currency flights" with other CFIs so that they could go up and get some experience in the above mentions conditions. I've also done night currency flights with CFIs who have never landed with their landing and taxi lights off. I make them do it, and BAM another drop into the experience bucket. In my view, we will all be learning something about flying until the day they pry that medical certificate from our fingers. As long as you respect the weather and the airplane, there is great experience to be gained at all levels. Just make sure you've done your homework, and have multiple options. Every time I go into to the chiefs wanting to fly in some unusual conditions, I go in armed with multiple backup plans in case things get worse. To this day, I haven't had one of my requests turned down, but that's because even though I want my students to experience everything that they possibly can, I can still recognize when it's just not a good day to fly.
