Will my brother get his finances straightened out?

The querent is asking about her brother's finances, he is apparently in debt and having difficulty paying his expenses. One of these concerns the house owned by both of them, where he lives. Will she have to pay or will he be able to work out his situation so he can cover the property taxes?

She is Venus, retrograde, in gemini and on the cusp of her brother's partners.
Her brother is the 3rd, ruled by slightly reckless sagittarius, and Jupiter who is in his 2nd (from the 3rd). South node in his 1st house shows the difficulty he is in, and Jupiter retrograde in its fall in his money house shows us his money problems. However, Jupiter approaches a conjunction with pluto, and this exact conjunction normally indicates a plentiness and an abundance. Both Bill Gates and Warren Buffet have this conjunction in their natals.
However, pluto is also co-ruler of the querent's money house! So is the brother's abundant money coming from his sister?
The ruler of the brother's 2nd is Saturn, retrograde in the second, again testimony to the scarcity of funds. However, ascendent ruler Venus by retrograde is approaching a trine with Saturn... again, is this her bailing him out?
The 4th from the brother's house, the house where he lives but is co-owned by the querent, has mars, the significator of the querent's ruler. Again, is this her money going towards the house?
Interesting that asteroid fortuna is conjunct Neptune here, and the brother is a pisces!
Moon's next aspect will be a trine to the fortuna/netpune conjunction.
I've inserted some asteroids, this is a family matter so Karma seems suitable, and it is conjunct the north node, in the house of the brother's partner (he is not married or seeing anyone).
The asteroid tyche of good luck is exactly semi-sextile mercury, and exactly square asteroid Ganesa, of successful new beginnings, in the sister's 2nd house.
Sun is exactly conjunct north node, ruler of her 11th and his 9th. Part of fortune in the ascendent exactly trines the sun/north node/karma conjunction.
I'm undecided, the aspects seem to swing both ways, What do you think?

The debt he is in would be Cancer 8th from 3rd where moon is posited. Moons in a pitted degree and is applying to oppose him Jupiter. Mars (his L5) has been in a past sextile with Jupiter. Has he been doing any 5th house activities to put himself in debt?

With SN in his asc house, his L2/saturn in a pitted degree, and his L8/moon in a pitted degree, with the moon in the opposite sign to him and still applying to him/jupiter, then i don't see any improvement right now.

I've added in his part of debt, which falls at 24° Taurus and is trine him/Jupiter in his cadent 6th house, once again in its in a pitted degree. Him/Jupiter retrogrades away from the debt but L1/venus is the one that flows towards the debt 24° Taurus.

Also, i forgot to mention he is in his 12th house of self-undoing and restrictions. There won't be much positive action being taken from this house.

Thanks, Chrysalis.
As far as she knows no 5th house money matters.
If we take the natural 4th as the co-owned house, he is there, with his money significator, Saturn.

"he is in his 12th house of self-undoing and restrictions."

Sorry, how did you get this? I'm not following.

I calculated some Parts, to shed some more light on this.

Part of Ancestral Heritage is at 20 sagittarius, in his house, and square Neptune. Not promising for the querent.

Part of Bankruptcy is at 5 sagittarius exactly opposite Venus, ruler of the querent (!).

Part of Debt is at 25 Pisces, conjunct mars, ruler of the querent's 2nd house (!).

Part of Siblings is 17 libra, square moon on MH.

It looks more and more as though she is going to have to pay out.

ElenaJ said:

"he is in his 12th house of self-undoing and restrictions."

Sorry, how did you get this? I'm not following.

Click to expand...

Oops sorry ive done it the opposite way around. His 12th would be Scorpio not cap. So him/Jupiter sits in his 2nd house.

Part of Bankruptcy is at 5 sagittarius exactly opposite Venus, ruler of the querent (!).

Part of Debt is at 25 Pisces, conjunct mars, ruler of the querent's 2nd house (!)

You need to calculate these from his house (3rd cusp).

The Part of Bankrupty is calculated with Jupiter+Neptune-Uranus, so it doesn't change.

The Part of Debt recalculated is at 22 Taurus, now in the querent's 8th, and trine the Jupiter/pluto conjunction in her brother's 2nd.

I'm really still undecided on the answer to this one. It seems 50/50.