Assalaamu alaykum wa rahmatullaahi wa barakaatuhu, Shaykh. I read the following:
It was narrated that Abu ‘Imraan Al-Jawni said:
“One of the Companions of Muhammad told me, when we were going out on a campaign towards Persia, ‘The Messenger of Allaah, sallallahu ‘alayhi wa sallam, said, 'If a person spends the night on a roof which has no surrounding wall, and he falls down and dies, no one is responsible for his death, and if a person travels by sea when it is stormy and dies, no one is responsible for his death.'’” Narrated by Imam Ahmad in his Musnad, 20224; classified as hasan by Al-Albaani.
My question, after reading this, is about travelling by air on a rainy or windy day and so on; will that person be of the same category if he dies in a plane crash or so? Or even if does not die, will he be sinful for boarding a flight in such weather? If yes, then what about a situation in which the flight was pre-booked and the climate conditions were not expected to be such, can a person board that flight? What if there is no re-fund or ticket exchange for another flight? May Allaah reward you, Shaykh.

All perfect praise be to Allah, The Lord of the worlds. I testify that there is none worthy of worship except Allah and that Muhammad, sallallahu ‘alayhi wa sallam, is His slave and Messenger. 

The hadeeth forbids traveling by sea if it gets rough as it is most likely unsafe in that case. However, when traveling by sea is most likely safe, it is permissible to travel. Ibn Hajar wrote, “It is deduced from the hadeeth that the forbiddance is confined to the sea getting rough (during stormy weather), and it is thus understood from it that it is permissible in the absence of the sea being rough. This is the famous scholarly view in this regard. If safety is most likely ensured, then traveling by sea is just like traveling by land.” [Fat-h Al-Baari]

As for airplanes, we did not find any contemporary scholar who held that it is forbidden to travel by air in certain weather conditions. The aforementioned ruling regarding traveling by sea applies to traveling by air as well; it is allowed when safety is most likely ensured. The layperson may not be able to judge what affects the safety of aircraft routes; this matter is left to be decided by experts in the field of navigation and weather. It is sufficient for the layperson to rely on their judgment in this regard. It is known that aviation authorities all over the world are extremely cautious regarding the safety of air travel.

Based on that, we deduce that your question with all its sub-points is more like a far-fetched hypothetical assumption.

Allah knows best.