Seems most of the discussion here is about glow powered planes, so let me toss in something electric and sailplanes.

We were recently at an Aerotow for large scale sailplanes. Winds were 15 mph gusting to 25 mph. The runway was directly into the wind. We had some big gas tow planes and 3-5 meter scale sailplanes. No one was flying.

Out I walk with my Aerobird (I hear the groans) and hand toss the plane up. Climb to about 300 feet or so, loops and such, then I take it down wind about 200 feet and cut the motor. From there I glided the plane into a landing right at my feet. Next thing you hear is motors starting and gliders being prepared for flight. Someone had to go up and test the conditions to see what was happening up there. The group flew the rest of the day with only one two minor misshaps, both on landing approach.

The only reason I would put up a small light plane like that in such wind is that over the last two seasons I have gradually taken it up in more and more wind. In addition, the plane is very tough so if a gust flips it on landing, the probabiliy of serious damage is small. So I can afford to take some risks with it.

Over the past two seasons I have also become a sailplane pilot. We often fly in 15-20 mph winds without a motor. So I have developed skills and confidence to deal with, and even work with the wind without the benefit of motor. I find it fun to fly in the wind. But it does involve risks as gusts will do things to you on approach that you can't control and can't overcome. Landing with more speed, especially with an unpowered sailplane is a must because a gust can take away all your energy reserve.

If you want to challenge the wind, you have to be willing to accept that risk, and that is probably the key item. How much risk are you willing to take with this individual plane in order to take on the challenge and develop the skills of flying in the wind.

For most experienced pilots I think it is not a matter of skills or the capability of the plane, but the risk and is it worth it.