Thanks for posting a link to your chart--it makes things quite a bit easier
Your natal Jupiter is tightly conjunct the second house cusp, so I'd consider it to be in the second house and not the first without a shadow of a doubt, and since the Sun is conjunct Jupiter, I think I'm leaning more towards the second house than the first house--although, again, I don't want to force any specific interpretation on you.
The Sun and Jupiter right on the second house cusp seems like a winning combination for financial matters to me, even if the Sun is in the sign of its fall in Libra. I'm not quite sure how Pluto conjunct Jupiter will affect this interpretation, though, because Pluto is the modern ruler of the eighth house, which is commonly associated with other's people's money.
Please don't take my word for the ultimate authority because I do not have much experience with these things, but I think it is very interesting that Jupiter is conjunct the Sun-Pluto midpoint right on the second house cusp. The first thing I thought when I saw this combination was perhaps you will gain some money through an inheritance, but since I've never personally studied charts with the intention of finding such influences, please do not bank too much on this.
I'm curious what unukalhai has to say about this midpoint--she has much more experience working with them than I do.
I'm also interested in your out-of-sign conjunction between Uranus in Scorpio and Venus in Sagittarius in the third house as well as Neptune tightly conjunct your Sagittarius Nadir.
There's also a yod configuration which consists of your twelfth house Mars in Leo sextile your second house Pluto in Libra, both quincunx your seventh house Moon in Pisces. Most of the yods I've seen have the generational Neptune-Pluto sextile as the base, so I'm curious how this particular configuration may be different with Mars and Pluto as the base. Mars and Pluto are sort of similar in that Pluto is considered to be the "higher octave" of Mars by some astrologers, and both planets rule the sign of Scorpio. Mars and Pluto "get along well" in your chart since they are both sextile each other, but the Moon is having a more difficult time as the apex planet of the yod, receiving the combined energies. The Finger of God is pointing at your Pisces Moon, my friend; use it well!
To make things more interesting, Pluto is in the "cross-fire" of your Cancer North Node-Capricorn South Node axis. Here's what
Pluto square North Node has to say about this aspect:
This square indicates a tendency to want to reform social and cultural philosophies and institutions. Thus, the natives will be at odds with the established order and will incur its disfavor. Depending on other factors in the horoscope, this can be either mild disapproval or a matter of life and death, in which the natives are regarded as dangerous revolutiojnaries by their society.
I'm still trying to make sense of this all, but I believe the Moon is emphasized in your chart because it is the ruler of your Cancer North Node and the apex planet of a yod configuration; clearly, this is the direction the Universe is indicating you must go in to continue your spiritual development. I've always thought of the Moon as being strong in Pisces even though it doesn't have any particular dignities such as rulership or exaltation; it's a water sign, but interestingly, the only water sign of the three that have a particular relationship with the Moon--either good or bad (i.e. Cancer is the sign of the Moon's rulership and Scorpio is the sign of the Moon's fall). Speaking of exaltation, your Saturn--the ruler of your Capricorn South Node--is exalted in Libra, so I believe the scales of Libra will be sort of unbalanced in favor of your South Node, since its ruler is more strongly placed. It is the natural tendency to be more "stuck" in the South Node because this is the mode of behavior that is familiar with us, but as I said earlier, your chart is clearly indicated that you must move in the opposite direction--develop your sense of trust, especially in your friends and in your "hopes and wishes" (eleventh house influences).
Arian Maverick