Is Venus square Jupiter actually a difficult aspect?

It is a hard aspect by geometry, and the difficulty is real, but it is not felt as friction. It is felt as agreement, which is precisely why it goes uncorrected for so long.

Does it show up in money as well as in love?

Venus is also the part of a chart that decides what a person finds worth paying for, so the same pattern turns up in spending as readily as in affection. Whether it becomes a problem depends on what else in the chart keeps accounts.

Is more always the answer here?

It is usually the first answer, and often a good one. What this configuration rarely supplies on its own is the moment where more stops being the answer.

Aspect

Venus square Jupiter

Venus square Jupiter is appetite running slightly ahead of proportion. Venus decides what registers as worth having. Jupiter is the planet the tradition assigns expansion and opportunity, and expansion applied to a preference does not make the preference wiser. It makes it larger.

It is the pleasantest of the hard contacts to carry, and it is still a hard contact. Nothing here hurts on the way in.

The two agree more than they argue

Jupiter is a social planet, and what is formally assigned to it is expansion and opportunity — the widening of a platform, the enlarging of a prospect. None of that is about love, and that matters: what this contact does to affection is not a rule about affection. It is a general habit of increase arriving at one specific appetite.

The two are old company. Jupiter is at home in Pisces, which is the sign where Venus is exalted, and Virgo is where Venus is said to be at its weakest and where Jupiter is held to be out of place as well. They agree, of all things, about what they find difficult. So a square between them is not an argument about direction. It is a disagreement about how much.

That is why the difficulty is so easy to miss and so expensive when it lands. A square between two bodies that want the same thing does not produce doubt. It produces momentum, and momentum only shows its cost at the far end — the promise made warmly and honoured with effort, the generosity that turns out to have been an advance on something.

How it tends to show up

Generosity that is genuine, immediate, and occasionally larger than the circumstances.

Enthusiasm for a person that outruns acquaintance and outlives the reasons for it.

Taste that is expansive rather than exact — more of the good thing, rather than the better one.

Promises made in good faith at the warmest moment of an evening.

What changes the reading

A square’s margin is wide, and a wide one here is barely a friction at all. The close contacts are the ones that show as scale.

Jupiter moves faster than the outer bodies and far slower than Venus, so its sign still says more about a year of births than about a person. The house is where the enlargement is aimed.

Whatever in the chart supplies proportion decides whether this reads as warmth or as overshoot. Without it there is nothing here that says stop, because neither of these two has ever been given that job.

Questions

Is Venus square Jupiter actually a difficult aspect?: It is a hard aspect by geometry, and the difficulty is real, but it is not felt as friction. It is felt as agreement, which is precisely why it goes uncorrected for so long.
Does it show up in money as well as in love?: Venus is also the part of a chart that decides what a person finds worth paying for, so the same pattern turns up in spending as readily as in affection. Whether it becomes a problem depends on what else in the chart keeps accounts.
Is more always the answer here?: It is usually the first answer, and often a good one. What this configuration rarely supplies on its own is the moment where more stops being the answer.