Hi Pix,
This is a very challenging chart, so I would like to have a go.
Robert is the fourth cusp which is at the beginning of Pisces, so he is Jupiter.
Jupiter is peregrine, having no essential dignity where he is, and having no mutual reception with another planet, so he drifts aimlessly and lacks standing. Physically, he is in the radical twelfth, a place of captivity and self-undoing, which added to his peregrine state describes him as feeling trapped and isolated. He approaches conjunction with the Ascendant, so he features heavily upon your own mind and this Ascendant is also his turned tenth, so he features also heavily upon his mothers.
Grandma is Mercury, and here she is also peregrine, so also wandering in a place in which she has no footing, and so both of them feel lost in terms of this situation. Mercury approaches conjunction with Jupiter, and although Mercury is in Jupiter's term, expressing Grandmas concern for Robert, also indicated by her application to conjoin him, Jupiter is in none of Mercury's dignities, suggesting that despite Grandma's concern for Robert, that he is rather indifferent toward her. Mercury, in Jupiter's term and applying to conjoin with Jupiter as observed, occurs within Grandma's turned third house, so this suggests an attempt of hers to communicate with him, make steps toward him, appeal to him, but his indifference makes this difficult, although he is very much aware of her, as he is in her turned tenth house (is he literally in her house?).
As for the money which is being given to Robert by his mother, then we look to Grandma's second, of her finances, and to Robert's eighth, of other people's resources, and see that both are represented by the tenth cusp, so Grandma's money that is given to Robert is represented by Venus. Venus is in it's domicile in Libra, so as the money is described as being strong, then I would imagine that it is a lot of money we are concerned with here, but the money is combust by the Sun, so we see that whatever is happening to this money, it is being burned up rather quickly, but we do not see what is burning this money up, because Leo, subject of the Sun, rules no cusp, so we must look elsewhere later on to see how this money is being spent.
Jupiter and Venus are mutually receptive by term, so he needs the money, he is bonded with it, there is a real need for this resource, but Jupiter is also in Venus' detriment, so at the same time, despite the fact that this money is depended upon Robert hates it, despises his need for it, suggesting that he would rather not have it but he is dependent upon it. The mother, Also in Venus' detriment also hates the money, so we can see how this cash causes much unease between the two. So what is it being spent upon?
Venus separates a harsh aspect from Luna in Cancer, which not only is a further description of how this money originates from his mother, but as Luna is the ruler of Robert's turned sixth, indicates how the need for this money originates in some sort of infirmity or disorder of Roberts. Venus' next aspect is a trine to Neptune, who rules altered states of conciousness and furthermore, is in Roberts twelfth house of bondage and attachment, so your speculations that Robert is spending this cash to fuel a drug addiction would seem to hold weight in the chart.
The ruler of the Robert's twelfth house of shackles and addiction is Saturn, which itself is natural significator of ties which cannot be broken and appears in his sixth of weakness and affliction. As Jupiter applies a close fixed square aspect to Saturn, then I imagine that a drug addiction is probably outlined here, but Saturn and Jupiter bear no recepetion, so obviously Robert and the addiction have no inclination toward each other, but as both planets are in Venus' terms, it is the money that bring them together, and indeed, make the bond possible between them in the first place. Saturn appears in Grandma's turned twelfth, so perhaps she knows nothing of this. Incidentally, Neptune which I described earlier, is in the domicile and exaltation of Saturn.
Admittedly my knowledge and deftness at interpreting charts is limited, but if I had to draw a conclusion I would suggest that Robert is not merely burning this money up, which he hates but yet needs, on minor drugs such as booze and weed, but upon something to which he is physically addicted and for which the money is a necessity in order to feed the addiction and settle his debts.
The Moon in Cancer is general significator of the situation at large, and as it is in Cancer, tells us about how this chart relates the theme of the concern of mother's and the need for nourishment, which if Robert is feeding a drug habit is what this is about.
Luna is waning, and separating from Mercury, showing perhaps how Grandma's ability to help Robert as his mother is in decline, she is losing her will to continue to nourish him in the way she is. Luna is in the radical eighth, always a baneful place, showing us loss and anxiety. Luna translates light from Mercury to Venus, so provides the link between the mother and the money, but as we have seen Luna's light is in decline, taking with it the mother's willingness to provide. Luna is upon the very degree of exaltation of Jupiter, and as natural significator of mother's, particularly in Cancer, Grandma does indeed love Robert very much, but there is only so much help she can give and her willingness to do so is in decline. The exaltation of Jupiter by Luna may tell us that there is yet high hopes for Robert, and perhaps his mother's increasing unwillingness to continue providing for him will be the best thing for him in the long run.
