The disruption to peoples plans and the expenses which are incurred make it a really difficult.
What does not help these days is the way the weather is reported. Yesterday I had a really good day sailing. Quite a lot of people were surprised and spoke of 100 mph winds being forecast.
Such winds were indeed forecast but for a relatively small area of Scotland and not until the evening. The forecast was for our area was that the rain would clear through and winds drop as a ridge of higher pressure passed us. And indeed that is what happened. The forecast wind was at the top end of force 4 but in fact turned out to be at the bottom end of Force 4.
The difficulty is that a difference of only 5 kts can make such a difference. At the NSSA Regatta in 2012 the fleets were coping at 16kts average windspeed. As soon as that went up to 18kts Race Officers were calling in saying the boats were not coping and we were abandoning racing.
The other difficulty is that, I suspect, most websites tend to go for a "worst case" probability when forecasting winds - and they can never be aware of local geographical considerations.
The other problem these days is that if something does go wrong you will face a trial by media and you can be sure that they will base their reporting on the headline forecast. So you tend to err on the side of caution.
And all of this has to be done beforehand and everyone has an opinion. Not at all easy!