I think the Trump and Vanderbilt lessons are that a well-positioned Jupiter isn't necessarily trouble-free. Buffet, interestingly, has Saturn in his second house. Despite Buffet's wealth, he is known for his frugal lifestyle and philanthropy; unlike Trump.
I wouldn't say that planets in signs or planets in houses are irrelevant. It's more like, if I somehow had to choose only one astrological method to use, it would be looking at aspects.
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Many different factors go into whether a person will be wealthy, very wealthy, poor or dirt poor.
Many people have morals & ethics & will not engage in illegal means to obtain wealth; others like the Dems I've mentioned, have no
qualms about doing just about anything to get money & power.
There are many ways to get rich, the drug cartels make billions & their charts will all be very different & not reliant on one aspect such
as you have attributed to Trump with Jupiter retrograde 2ND. That hasn't prevented him from becoming one of the wealthiest men in
America. That formidable Mars-Regulus & he picks himself up, dusts himself off & carries on winning!
Buffet is a complete fraud; the very wealthy have 'charitable or trust funds' to avoid paying taxes. It's justa scam for them while
pretending to be philanthropists.
Trump has given more money away than Buffet but he does it privately, without publicity. He made his inheritance grow throough
his 'Trump brand' of hotels, golf courses & resorts & his t.v. fame came after he was already a very successful businessman.
Bankruptcy not uncommon with very large businesses, nothing to do with Jupier 2ND which is growth & expansion & where
Orange Man finds his 'luck'. Trump made his own ' luck' by working very hard & never giving up.
Venus is the planet more likely attributing to whether one will be 'comfortable in life' as in rich as it rules physical objects & money
is needed to buy big homes, diamonds & other luxurious items.
Would it surprise you to know which two sun signs are the wealthiest?
If you really want to understand wealth in a chart, look to the houses of money, look to their Venus & the sign & aspects but you also
need to look at their Luminaries to see whether they have 'character' or not'. A person with an afflicted Sun Moon COULD be lacking in
principles or emotions which would gear them towards crime & illlegit gains.
There are NO markers in a chart that show up in charts of criminals for it's all based on motives & what lies in a person's heart.
A chart can tell us the wealth potential but cannot tell us whether that person will obtain their wealth legally or illegally, morally or
immorally. The nicest, kindness people tend to be poor, just like 99% of the world. Nothing to do with astrology but a rigged, gamed
system with one rule for the 1% & another rule for the 99%. Blaming the victim for their own poverty is a trick used by the elites in
order for them to keep stealing, scamming, deceiving & lying to get rich. Neptune once again rears her head with their total lack of
transparency. Saturn with their control over all the institutions which serve THEM & not the people.
Astrology gives information about a natal chart based on houses, signs, aspects but it does not give information about motive,
ethics, morality.