I have found that Jupiter transits, especially conjunctions, to Sun or Moon can bring little breaks, though so far, no actual jackpots. (Astrocartography suggests you should play the lottery at a place in the world where your Jupiter-Pluto lines cross, in case that question is in anyone's mind. I have no wish to claim its possible infallibility, though. The root meaning of the word word 'Pluto' is 'wealth.' Actually, my Jupiter-Pluto lines cross at San Fran Cisco. Well, I did met Jupiter-Pluto there virtually, over the internet. It is the sense that there are many extreme believers there that made the biggest impression on me, each planet magnifying the excesses of the other to undue proportions. At least, that is how it came across to me.)
Transit Jupiter to Sun: found a flat, when I needed a new place to live urgently. That happened once. Jupiter to Moon: I got a cut-price trip to Venice at the last minute. The travel agents spluttered a little bit to begin wth when I asked them if they had any cheap flights for me that day, but they did deliver. Transit sextils and trines do seem to give a sense of 'flow' and well-being and it does seemto be easier for opportunities to happen here.
A welcome break also became manifest on my most recent Jupiter return, though this by no means was not the case on the previous two occasions. This had been in he pipeline for som months before, but when this transit was more or less exact, a limited edition of some Tarot cards did come out, along with some royalties.
So I do think it it worth paying attention to Jupiter transits, though Uranus is also a planet I could associate with breaks. For me, Saturn very firmly squares my Midheaven, so it is good to remember that it does not always have to be about what can and often does manifest with the former in terms of rejection and more rejection of various ouvres.