Re: Financial Windfall
This is an interesting one. Jupiter on your dad's 8th cusp is the first thing that leap out at me. The trine from t Jupiter could have led to that windfall. I also notice the South Node crossing over that natal Jupiter. Comparing this to my chart, I also had a financial windfall recently - two aspects similar involving 2nd, 8th house and their rulers. Tr Jupiter trine natal Saturn, the ruler of my natal 2nd house, tr South Node conjunct natal Saturn.
I also recently had the transit of nodes across the 2nd/8th axis so lots of lessons regarding money/values. Actually I have very similar ascendant degree/sign to your dad. I am guessing, when the nodes are finished in the houses they recently transit through, perhaps they leave some sort of gift - but that is my theory that I'm looking into. South node in my 8th, I had to borrow a LOT of money, then when exiting the 8th, I win a LOT of money!
South node I have found, can perhaps draw out of the planet whatever it rules/represents. South node could have drawn out money (2nd house) from my natal Saturn from ex employer (Saturn/work).
Perhaps the Full Moon in Libra, 9 degree, opposite his natal Moon (8th ruler) and trine his Saturn (2nd house ruler) triggered that also. I wonder if the natal promise has something to do with the Venus in his 8th sextile the Saturn (2nd ruler), which could have been triggered also by the lunation.
Anyways, good luck, very good news for your dad!