I'd just like to point out that today the quality of weather service is more than adequate to provide info about what kind of head or tailwind to expect. Not with 100% accuracy, but those services ARE plenty good enough that you NEVER should be caugth by surprise by an unexpected headwind.

The needed weather info is there, but is it available in a format, way and form that a particular pilot can relate to? There is still much work to be done when it comes to this kind of weather service.

In a perfect world the winds at your flight level would enter your ground speed calculations automagically. I've seen some proprietary systems where they have this kind of functionality (Jeppesen flight planner, although the user interface for this function was possible one of the worst possible I've ever seen). Proprietary also meant that the system was tied and locked to a particular weather service provider. There's nothing wrong with that particular w.s. provider, but we can't accept that kind of proprietary tie-in.

I'm not a pilot, but I am a weather forecaster that has transformed into something between a geographer and IT consultant. I am working on developing exactly the kind of services and infrastructure for this kind of services for our military.