As a typical member of the neutral evil alignment, the Dark Prince Greya clearly did not act as freely and haphazardly as his sister.
After arriving in Fuyuki City, he did not rush to cause trouble for Little Annie. Instead, he first obtained a legal identity for himself, then acquired several businesses as an investor, transforming himself into a member of this world's upper class.
In particular, nearly every ice cream shop, dessert shop, restaurant, and similar establishment frequented by Little Annie had been acquired through one means or another.
He then quietly installed surveillance cameras made with Phyrexian Oil, technology far beyond this world's level, throughout those establishments.
That way, Greya could monitor his sister's every move without alerting anyone.
Not only that, he also acquired Fuyuki City's largest taxi and freight companies, as well as various sufficiently tall landmark buildings, secretly installing vast numbers of surveillance cameras on them.
In the end, he used these cameras to construct an enormous, comprehensive three-dimensional network with virtually no blind spots.
Any Master or Servant who left their base would immediately appear on the large screens in the surveillance room. Even during pitch-black nights, the night vision function would capture them with perfect clarity.
Even Kiritsugu Emiya and his assistant and lover, Maiya Hisau, had no privacy whatsoever when they hid in their room to engage in intimate acts.
Moreover, because no magecraft or magic was used at all and this was purely a technological advantage, it would not trigger the magical barriers designed specifically against such things.
Thus, in less than a day, the Dark Prince had established an intelligence system that most people in this world could not even imagine.
As for where the money came from...
Rather than simply and crudely printing money or creating gold like Little