It is easy to sound elitist in forums
but (a) I don't think planning a flight is in any way difficult (these days, any chimp with a laptop and an internet connection should know how to plan a flight from say Bournemouth to say Casablanca) and (b) I would not trust somebody else to do the weather planning for me.
In the high-end bizjet and airline world, the pilot is handed a pre-planned package and he just flies, like a bus driver. That is done
- to save time
- the aircraft are massively capable machines, fully de-iced, with radar, and with a 99.x% despatch rate, so the chance of the pilot looking at the wx and saying he doesn't want to fly is close to zero (and he might get the sack if he did that and the wx was above the minima in the approved ops manual
)
- the routes are often long enough to require complicated overflight permit arrangements which could take days to sort out
At the lower end of the bizjet world, the pilot has to do it all himself.
The weather decisions, for a relatively much less weather-capable aircraft like most of us fly, are much more individual. For example, I don't fly in IMC enroute on high altitude IFR, because airframe icing is almost guaranteed, eventually, but there are conditions where I would do that, like when the "IMC" is just a haze, and I use the IR satellite images to evaluate that. OTOH some pilots would just drill through anything; and usually they survive. Climbing and descending through icing layers is another one, where I am not going to have somebody else telling me what I can do or not.