Regarding the change from verb to preposition, I think the process was as follows:
"The wind notwithstanding, the house survived." Here "notwithstanding" is a (negatived) present participle, and "the wind notwithstanding" is an absolute (i.e. detached) clause. It corresponds to the Latin ablative absolute construction ("non obstante" is in the ablative case).
Word order in Latin is freer than in English, so "non obstante" would often (perhaps usually) be placed before its subject noun. Since "notwithstanding" was a formal/legal term in English, there would be a tendency for its usage to imitate the Latin word order. So one might say "Notwithstanding the wind..." (verb + subject). But this word order was unusual in the context of English as a whole, so ordinary people would tend to interpret "notwithstanding" as a preposition when it was placed first. Eventually, it achieved "official" status as a preposition.
"Withstanding" should be taken as meaning "standing firm". So "notwithstanding the wind" means "the wind not standing firm". The wind was "broken" by the house.
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